2-benzoylcyclohexane-1,3-dione as herbicides

ABSTRACT

2-Benzoylcyclohexane-1,3-diones of formula I :                    
     where: 
     R 1  and R 2  are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, alkyl, haloalkyl, alkoxy, alkenyl, alkynyl, —OR 3 , —OCOR 3 , —OSO 2 R 3 , —S(O) n R 3  (n=0, 1, 2), —SO 2 OR 3 , —SO 2 N(R 3 ) 2 , —NR 3 SO 2 R 3  or —NR 3 COR 3 ; 
     R 3  is hydrogen or optionally substituted alkyl, haloalkyl, alkenyl, alkynyl, phenyl or phenylalkyl; 
     Q is optionally substituted cyclohexane-2-yl-1,3-dione; 
     X 1  is optionally substituted alkylene, propenylene, alkenylene or alkynylene; 
     R 4  is hydrogen or optionally substituted alkyl, alkenyl, alkynyl, phenyl, phenylalkyl; 
     Het is a three- to six-membered, optionally substituted heterocyclic or heteroaromatic group; 
     and agriculturally useful salts thereof, processes and intermediates for preparing compounds of formula I, compositions comprising them, and the use of the compounds of formula I and the compositions comprising them for controlling harmful plants are described.

The present invention relates to substituted2-benzoylcyclohexane-1,3-diones of the formula I:

where:

R¹ and R² are each hydrogen, mercapto, nitro, halogen, cyano,thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl,C₂-C₆-alkynyl, —OR³, —OCOR³, —OSO₂R³, —S(O)_(n)R³, —SO₂OR³, —SO₂N(R³)₂,—NR³SO₂R³ or —NR³COR³;

R³ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl; where the abovementionedalkyl radicals may be partially or fully halogenated and/or may carryone to three of the following groups:

hydroxyl, mercapto, amino, cyano, R³, —OR³, —SR³, —N (R³)₂, ═NOR³,—OCOR³, —SCOR³, —NR³COR³, —CO₂R³, —COSR³, —CON(R³)₂,C₁-C₄-alkyliminooxy, C₁-C₄-alkoxyamino, C₁-C₄-alkylcarbonyl,C₁-C₄-alkoxy-C₂-C₆-alkoxycarbonyl, C₁-C₄-alkylsulfonyl, heterocyclyl,heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy andhetaryloxy, where the eight last mentioned radicals may in turn besubstituted;

n is 0, 1 or 2;

Q is a cyclohexane-1,3-dione ring with or without substitution which isattached in position 2;

X¹ is a straight-chain or branched C₁-C₆-alkylene, a C₂-C₆-alkenylene ora C₂-C₆-alkynylene chain which is interrupted by a hetero atom selectedfrom the group consisting of:

oxygen or sulfur,

where the abovementioned alkyl, alkenyl or alkynyl radicals may bepartially halogenated and/or may carry one to three of the followinggroups:

—OR⁴, —OCOR⁴, —OCONHR⁴ or —OSO₂R⁴;

is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl,phenyl-C₁-C₆-alkyl, where the abovementioned alkyl, alkenyl or alkynylradicals may be partially or fully halogenated and/or may be substitutedby one or more of the following radicals:

hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁-C₄-alkylamino,C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl,C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio,C_(l)-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;

Het is a three- to six-membered partially or fully saturatedheterocyclic group or a three- to six-membered heteroaromatic grouphaving up to three hetero atoms selected from the following threegroups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may bepartially or fully halogenated and/or may be substituted by R⁵;

R⁵ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl,C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C_(l)-C₄-alkoxycarbonyl,C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, where the alkyl radicals may in each case besubstituted by in each case one or more of the following radicals:

cyano, formyl, C_(l)-₄-alkylamino, C₁-C₄-dialkylamino,C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C_(l)-₄-alkylcarbonyloxy,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;

and agriculturally useful salts thereof.

In addition, the invention relates to processes and intermediates forpreparing compounds of the formula I, to compositions comprising themand to the use of the compounds of the formula I and to compositionscomprising them for controlling harmful plants.

2-Benzoylcyclohexane-1,3-diones are disclosed in the literature, forexample in EP-A 278 742, EP-A 298 680, EP-A 320 864 and WO 96/14285.

However, the herbicidal properties of the prior art compounds and theircrop plant safety are not entirely satisfactory.

It is an object of the present invention to provide novel, in particularherbicidally active, compounds having improved properties.

We have found that this object is achieved by the2-benzoylcyclohexane-1,3-diones of the formula I and their herbicidalactivity.

Furthermore, we have found herbicidal compositions which comprise thecompounds I and have very good herbicidal activity. Moreover, we havefound processes for preparing these compositions and methods forcontrolling unwanted vegetation using the compounds I.

The present invention also provides stereoisomers of the compounds ofthe formula I. Pure stereoisomers and also mixtures thereof areincluded.

Depending on the substitution pattern, the compounds of the formula Imay contain one or more chiral centers and, if this is the case, arepresent as mixtures of enantiomers or diastereomers. The inventionprovides the pure enantiomers or diastereomers and also mixturesthereof.

The compounds of the formula I may also be present in the form of theiragriculturally useful salts, the kind of salt generally not beingimportant. The salts of those cations or the acid addition salts ofthose acids whose cations or anions, respectively, do not adverselyaffect the herbicidal activity of the compounds I are generallysuitable.

Suitable cations are in particular ions of the alkali metals, preferablylithium, sodium and potassium, of the alkaline earth metals, preferablycalcium and magnesium, and of the transition metals, preferablymanganese, copper, zinc and iron, and ammonium, where, if desired, oneto four hydrogen atoms may be replaced by C₁-C₄-alkyl orhydroxy-C₁-C₄-alkyl and/or one phenyl or benzyl, preferablydiisopropylammonium, tetramethylammonium, tetrabutylammonium,trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions,preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferablytri(C₁-C₄-alkyl)sulfoxonium.

Anions of usable acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and the anions of C₁-C₄-alkanoic acids,preferably formate, acetate, propionate and butyrate.

Emphasis is given to the compounds of the formula I according to theinvention where the variable Q is a cyclohexane-1,3-dione ring of theformula II

which is attached in position 2, where II may also represent thetautomeric formulae II′ and II″,

where

R⁶, R⁷, R⁹ and R¹¹ are each hydrogen or C₁-C₄-alkyl;

R⁸ is hydrogen, C₁-C₄-alkyl or C₃-C₄-cycloalkyl, where the two lastmentioned groups may carry one to three of the following substituents:

halogen, C₁-C₄-alkylthio or C₁-C₄-alkoxy; or

is tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl,tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl,tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl,1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or1,3-dithian-2-yl, where the 6 last mentioned radicals may be substitutedby one to three C_(l)-C₄-alkyl radicals;

R¹⁰ is hydrogen, C_(l)-C₄-alkyl or C₁-C₆-alkoxycarbonyl; or

R⁸ and R¹¹ together form a π bond or a three- to six-memberedcarbocyclic ring; or

the CR⁸R⁹ unit may be replaced by C═O.

Process A

Reactions of the cyclohexane-1,3-dione of the formula II with anactivated carboxylic acid IIIa or a carboxylic acid IIIb, which ispreferably activated in situ, to give the acylation product IV, andsubsequent rearrangement to the compounds of the formula I according tothe invention.

L¹ is a nucleophilically replaceable leaving group such as halogen, forexample bromine or chlorine, hetaryl, for example imidazolyl or pyridyl,or carboxylate, for example acetate, trifluoroacetate, etc.

The activated carboxylic acid can be employed directly, as in the caseof acyl halides, or be generated in situ, for example by usingdicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic esters,2-pyridine disulfid/triphenylphosphine, carbonyldiimidazole, etc.

It may be advantageous to carry out the acylation reaction in thepresence of a base. Starting materials and auxiliary base areadvantageously employed in equimolar amounts. A slight excess ofauxiliary base, for example 1.2 to 1.5 molar equivalents, based on II,may be advantageous under certain circumstances.

Suitable auxiliary bases are tertiary alkylamines, pyridine or alkalimetal carbonates. Examples of solvents which can be used are chlorinatedhydrocarbons, such as methylene chloride, 1,2-dichloroethane, aromatichydrocarbons, such as toluene, xylene, chlorobenzene, ethers, such asdiethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polaraprotic solvents, such as acetonitrile, dimethylformamide, dimethylsulfoxide, or esters such as ethyl acetate, or mixtures of these.

If acyl halides are employed as activated carboxylic acid component, itmay be advantageous to cool the reaction mixture to 0-10° C. when addingthis reaction partner. The mixture is subsequently stirred at 20-100°C., preferably at 25-50° C., until the reaction is complete. Work-up iscarried out in a customary manner, for example by pouring the reactionmixture into water and extracting the product of value. Solvents whichare particularly suitable for this purpose are methylene chloride,diethyl ether and ethyl acetate. After the organic phase has been driedand the solvent has been removed, the crude enol ester of the formula IVis purified, preferably by chromatography. Alternatively, it is possibleto employ the crude enol ester of the formula IV without furtherpurification for the rearrangement reaction.

The rearrangement of the enol esters of the formula IV to the compoundsof the formula I is advantageously carried out at from 20 to 40° C. in asolvent and in the presence of a base and, if appropriate, in thepresence of a cyano compound.

Examples of solvents which can be used are acetonitrile, methylenechloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene ormixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines such as triethylamine, pyridine oralkali metal carbonates such as sodium carbonate, potassium carbonate,which are preferably employed in equimolar amounts or up to a four-foldexcess, based on the ester. Preference is given to using triethylamineor alkali metal carbonates.

Suitable cyano compounds are inorganic cyanides such as sodium cyanide,potassium cyanide and organic cyano compounds such as acetonecyanohydrin, trimethylsilyl cyanide. They are employed in an amount of 1to 50 mol percent, based on the ester. Preference is given to usingacetone cyanohydrin or trimethylsilyl cyanide, for example in an amountof 5 to 15, preferably 10, mol percent, based on the ester.

Particular preference is given to employing alkali metal carbonates,such as potassium carbonate, in acetonitrile or dioxane.

Work-up can be carried out in a manner known per se. For example, thereaction mixture is acidified with dilute mineral acid, such as 5%strength hydrochloric acid or sulfuric acid, and extracted with anorganic solvent, for example methylene chloride, ethyl acetate. Theorganic phase can be extracted with 5-10% strength alkali metalcarbonate solution, for example sodium carbonate or potassium carbonatesolution. The aqueous phase is acidified, and the precipitate whichforms is filtered off with suction and/or extracted with methylenechloride or ethyl acetate, dried and concentrated.

The benzoic acids of the formula III are novel,

where:

R¹ and R² are each hydrogen, mercapto, nitro, halogen, cyano,thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl,C₂-C₆-alkynyl, —OR³, —OCOR³, —OSO₂R³, S(O)_(n)R³, —SO₂OR³, —SO₂N(R³)₂,—NR³SO₂R³ or —NR³COR³;

R³ is hydrogen, C_(l)-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl; where the abovementionedalkyl radicals may be partially or fully halogenated and/or may carryone to three of the following groups:

hydroxyl, mercapto, amino, cyano, R³, —OR³, —SR³, —N(R³)₂, ═NOR³,—OCOR³, —SCOR³, —NR³COR³, —CO₂R³, —COSR³, —CON(R³)₂,C₁-C₄-alkyliminooxy, C₁-C₄-alkoxyamino, C₁-C₄-alkylcarbonyl,C₁-C₄-alkoxy-C₂-C₆-alkoxycarbonyl, C₁-C₄-alkylsulfonyl, heterocyclyl,heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy andhetaryloxy, where the eight last mentioned radicals may in turn besubstituted;

is 0, 1 or 2;

X¹ is a straight-chain or branched C₁-C₆-alkylene, a C₂-C₆-alkenylene ora C₂-C₆-alkynylene chain which is interrupted by a hetero atom selectedfrom the group consisting of:

oxygen or sulfur,

where the abovementioned alkyl, alkenyl or alkynyl radicals may bepartially halogenated and/or may carry one to three of the followinggroups:

—OR⁴, —OCOR⁴, —OCONHR⁴ or —OSO₂R⁴;

R⁴ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl,phenyl-C₁-C₆-alkyl, where the abovementioned alkyl, alkenyl or alkynylradicals may be partially or fully halogenated and/or may be substitutedby one or more of the following radicals:

hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁-C₄-alkylamino,C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl,C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio,C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;

Het is a three- to six-membered partially or fully saturatedheterocyclic group or a three- to six-membered heteroaromatic grouphaving up to three hetero atoms selected from the group consisting of:

nitrogen, oxygen or

sulfur,

where the abovementioned heterocyclic or heteroaromatic group may bepartially or fully halogenated and/or may be substituted by R⁵;

R⁵ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl,C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl,C_(l)-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl,C_(l)-C₄-haloalkyl, C₁-C₄-alkylthio, C_(l)-C₄-haloalkylthio,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, where the alkyl radicals may in eachcase be substituted by in each case one or more of the followingradicals:

cyano, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino,C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;

R¹² is hydroxyl or a hydrolyzable radical.

Examples of hydrolyzable radicals are alkoxy, phenoxy, alkylthio andphenylthio radicals which possibly are substituted, halides, hetarylradicals which are bonded via nitrogen, amino and imino radicals whichpossibly are substituted, etc.

Preference is given to benzoyl halides IIIa where L¹=halogen({circumflex over (=)} III where R¹²=halogen),

where

R₁, R₂, X and Het are each defined under formula III and

L¹ is halogen, in particular chlorine or bromine.

Preference is also given to benzoic acids of the formula IIIb({circumflex over (=)} III where R¹²=hydroxyl),

where R¹, R², X¹ and Het are each as defined under formula III.

Preference is also given to benzoic esters of the formula IIIc({circumflex over (=)}III where R¹²=C₁-C₆-alkoxy),

where

R¹, R², X¹ and Het are each as defined under formula III and

M is C₁-C₆-alkoxy.

With regard to the preferred benzoic acids of the formula III, theremarks made under the 2-benzoylcyclohexan-1,3-dione of the formula Iapply to the radicals R¹, R², X¹ and Het.

The compounds of the formula IIIa (where L¹=halogen) can be synthesizedby methods similar to those known from the literature (cf. L. G. Fieser,M. Fieser “Reagents for organic Synthesis”, Vol. I, pp. 767-769 (1967))by reacting benzoic acids of the formula IIIb with halogenating agentssuch as thionyl chloride, thionyl bromide, phosgene, diphosgene,triphosgene, oxalyl chloride and oxalyl bromide.

The benzoic acids of the formula IIIb can be obtained, inter alia, byhydrolyzing the benzoic esters of the formula IIIc (whereM=C₁-C₆-alkoxy).

The benzoic esters of the formula IIIc according to the invention arepreparable by various methods known from the literature (for example a:G. Dittus in Houben-Weyl, Methoden der Organischen Chemie, Volume VI/3,Oxygen compounds I, 4th edition, p. 493 ff., Georg Thieme Verlag, 1965;b: T. L. Gilchrist, Heterocyclenchemie, 2nd edition, Verlag Chemie,1995) as illustrated in the examples that follow.

Process B

Substitution of the benzoic esters Va with suitable nucleophiles VIgives the benzoic esters IIIc according to the invention,

where M, R¹ and R² are each as defined above, L² is a suitablenucleophilically replaceable leaving group such as halogen, for examplebromine or chlorine, hetaryl, for example imidazolyl or pyridyl,carboxylate, for example acetate or trifluoroacetate, sulfonate, forexample mesylate, triflate, etc.,

X² is a straight-chain or branched alkylene, an alkenylene or aalkynylene chain having at least one and a maximum of five carbon atoms

where the abovementioned alkylene, alkenylene or alkynylene radicals maybe partially halogenated and/or may carry one to three of the followinggroups:

—OR⁴, —OCOR⁴, —OCONHR⁴ or —OSO₂R⁴ and

X³ is a straight-chain or branched alkylene, an alkenylene or analkynylene chain having a maximum of five carbon atoms

where the abovementioned alkylene, alkenylene or alkynylene radicals maybe partially halogenated and/or may carry one to three of the followinggroups:

—OR⁴, —OCOR⁴, —OCONHR⁴ or —OSO₂R⁴, where X²OX³ builds up the variableX¹.

In general, the starting materials are employed in equimolar amounts.However, it may be advantageous to employ an excess of one or anothercomponent.

If appropriate, it may be advantageous to carry out the reaction in thepresence of a base. The starting materials and the auxiliary base areadvantageously employed in equimolar amounts. In certain cases, anexcess of the auxiliary base, for example 1.5 to 3 molar equivalents,based on Va, may be advantageous.

Suitable auxiliary bases are tertiary alkylamines such as triethylamineand pyridine, alkali metal carbonates, for example sodium carbonate andpotassium carbonate, and alkali metal hydrides, for example sodiumhydride. Preference is given to using triethylamine, pyridine andpotassium carbonate.

Examples of suitable solvents are chlorinated hydrocarbons such asmethylene chloride and 1,2-dichloroethane, aromatic hydrocarbons, forexample toluene, xylene, chlorobenzene, ethers such as diethyl ether,methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aproticsolvents such as acetonitrile, dimethylformamide and dimethyl sulfoxide,or esters such as ethyl acetate, or mixtures of these.

The reaction temperature is generally in the range from 0° C. to theboiling point of the reaction mixture.

Work-up can be carried out in a manner known per se.

Process C

Substitution of appropriately substituted heterocycles VII with benzoicesters Vb gives the benzoic esters IIIc according to the invention,

where M, R¹ and R² are each as defined above, L² is a suitablenucleophilically replaceable leaving group such as halogen, for examplebromine or chlorine, hetaryl, for example imidazolyl or pyridyl,carboxylate, for example acetate or trifluoroacetate, sulfonate, forexample mesylate, triflate, etc.,

X² is a straight-chain or branched alkylene, an alkenylene or aalkynylene chain having at least one and a maximum of five carbon atoms

where the abovementioned alkylene, alkenylene or alkynylene radicals maybe partially halogenated and/or may carry one to three of the followinggroups:

—OR⁴, —OCOR⁴, —OCONHR⁴ or —OSO₂R⁴ and

X³ is a straight-chain or branched alkylene, an alkenylene or analkynylene chain having a maximum of five carbon atoms

where the abovementioned alkylene, alkenylene or alkynylene radicals maybe partially halogenated and/or may carry one to three of the followinggroups:

—OR⁴, —OCOR⁴, —OCONHR⁴ or —OSO₂R⁴,

where X²OX³ builds up the variable X¹.

In general, the starting materials are employed in equimolar amounts.However, it may be advantageous to employ an excess of one or anothercomponent.

If appropriate, it may be advantageous to carry out the reaction in thepresence of a base. The starting materials and the auxiliary base areadvantageously employed in equimolar amounts. In certain cases, anexcess of the auxiliary base, for example 1.5 to 3 molar equivalents,based on VII, may be advantageous.

Suitable auxiliary bases are tertiary alkylamines such as triethylamineand pyridine, alkali metal carbonates, for example sodium carbonate andpotassium carbonate, and alkali metal hydrides, for example sodiumhydride. Preference is given to using triethylamine, pyridine andpotassium carbonate.

Examples of suitable solvents are chlorinated hydrocarbons such asmethylene chloride and 1,2-dichloroethane, aromatic hydrocarbons, forexample toluene, xylene, chlorobenzene, ethers such as diethyl ether,methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aproticsolvents such as acetonitrile, dimethylformamide and dimethyl sulfoxide,or esters such as ethyl acetate, or mixtures of these.

The reaction temperature is generally in the range from 0° C. to theboiling point of the reaction mixture.

Work-up can be carried out in a manner known per se.

Emphasis is given to the compounds of the formula I according to theinvention where the group X¹ is either a C₁-C₂-alkylene or aC₂-alkenylene chain including one further oxygen or sulfur atom and

Het is a three- to six-membered partially or fully saturatedheterocyclic group or a three- to six-membered heteroaromatic grouphaving up to three hetero atoms selected from the group consisting of:

nitrogen, oxygen and sulfur,

where the abovementioned heterocyclic or heteroaromatic group may bepartially or fully halogenated and/or may be substituted by R⁵.

Additionally, emphasis is given to the compounds of the formula Iaccording to the invention where the group Het is a five- orsix-membered partially or fully saturated heterocyclic or a five- orsix-membered heteroaromatic group having up to three hetero atomsselected from the group consisting of nitrogen, oxygen and sulfur, wherethe abovementioned heterocyclic or heteroaromatic group may be partiallyor fully halogenated and/or be substituted by R⁵;

R⁵ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl,C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl,C₁-C₄-alkylcarbonyl, C₁-C₄alkyl-carbonyloxy, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, where the alkyl radicals may in each case besubstituted by in each case one or more of the following radicals:

cyano, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino,C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄alkyl-carbonyloxy,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄alkyl-thio, C₁-C₄-haloalkylthio,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy.

The organic moieties mentioned for the substituents R¹-R¹² or asradicals on phenyl, hetaryl and heterocyclyl rings are collective termsfor individual enumerations of the individual group members. Allhydrocarbon chains, ie. all alkyl, haloalkyl, cycloalkyl, alkoxyalkyl,alkoxy, haloalkoxy, alkyliminooxy, alkoxyamino, alkylsulfonyl,haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl,alkoxyalkoxycarbonyl, alkenyl, cycloalkenyl, alkynyl moieties can bestraight-chain or branched. Unless otherwise specified, halogenatedsubstituents preferably carry one to five identical or different halogenatoms, the meaning of halogen being in each case fluorine, chlorine,bromine or iodine.

Examples of other meanings are:

C₁-C₄-alkyl and the alkyl moieties of C₁-C₄-alkylcarbonyl: methyl,ethyl, n-propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyland 1,1-dimethylethyl;

C₁-C₆-alkyl and the alkyl moieties of C₁-C₆-alkoxy-C₁-C₆-alkyl andC₁-C₆-alkylcarbonyl: C₁-C₄-alkyl as mentioned above, and also pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and1-ethyl-3-methylpropyl;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, eg. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl,2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl,2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl,2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyland nonafluorobutyl;

C₁C₆-haloalkyl and the haloalkyl moieties of C₁-C₆-haloalkylcarbonyl:C₁-C₄-haloalkyl as mentioned above, and also 5-fluoropentyl,5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl,6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl anddodecafluorohexyl;

C₁-C₄-alkoxy and the alkoxy moieties of C₁-C₄-alkoxyamino,C₁-C₄-alkoxy-C₂-C₆-alkoxycarbonyl and C₁-C₄-alkoxycarbonyl: methoxy,ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy,2-methylpropoxy and 1,1-dimethylethoxy;

C₁-C₆-alkoxy and the alkoxy moieties of C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkoxy-C₂-C₆-alkyl, C₁-C₄ -alkoxy-C₂-C₆-alkoxycarbonyl andC₁-C₆-alkoxycarbonyl: C₁-C₄-alkoxy as mentioned above, and also pentoxy,1-methylbutoxy, 2-methylbutoxy, 3-methoxybutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and1-ethyl-2-methylpropoxy;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, eg. fluoromethoxy, difluoromethoxy, trifluoromethoxy,chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy,2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy,3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy,1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy,4-bromobutoxy and nonafluorobutoxy;

C₁-C₄-alkylsulfonyl (C₁-C₄-alkyl-S(═O)₂—): methylsulfonyl,ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl,1-methylpropylsulfonyl, 2-methylpropylsulfonyl and1,1-dimethylethylsulfonyl;

C₁-C₆-alkylsulfonyl: C₁-C₄-alkylsulfonyl as mentioned above, and alsopentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl,3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl,1-ethylpropylsulfonyl, 1,1-dimethylpropylsulfonyl,1,2-dimethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl,2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl,1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl,1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl,2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl,1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;

C₁-C₆-haloalkylsulfonyl: a C₁-C₆-alkylsulfonyl radical as mentionedabove which is partially or fully substituted by fluorine, chlorine,bromine and/or iodine, ie. fluoromethylsulfonyl, difluoromethylsulfonyl,trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl,bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl,2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl,2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl,2,2,2-trichloroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl,2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl,pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl,3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl,2-bromopropylsulfonyl, 3-bromopropylsulfonyl,2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl,heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl,1-(chloromethyl)-2-chloroethylsulfonyl,1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutylsulfonyl,5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl,5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl,6-iodohexylsulfonyl and dodecafluorohexylsulfonyl;

C₁-C₄-alkyliminooxy: methyliminooxy, ethyliminooxy, 1-propyliminooxy,2-propyliminooxy, 1-butyliminooxy and 2-butyliminooxy;

C₃-C₆-alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl,buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl,2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl,penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl,1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl,1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl,1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl,1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl,1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl,hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-1-en-1-yl,2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl,1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl,4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl,2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl,1,2-dimethylbut-3-en-1-yl, 3-dimethylbut-1-en-1-yl,1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl,2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl,3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl,1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl,2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl,1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl;

C₂-C₆-alkenyl: C₃-C₆-alkenyl as mentioned above, and also ethenyl;

C₃-C₆-alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl, but-1-yn-1-yl,but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-1-yl,pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl,pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl,3-methylbut-1-yn-4-yl, hex-1-yn-1-yl, hex-1-yn-3-yl, hex-1-yn-4-yl,hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl,hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl,3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl,3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yland 4-methylpent-2-yn-5-yl;

C₂-C₆-alkynyl: C₃-C₆-alkynyl as mentioned above, and also ethynyl:

C₃-C₆-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

C₄-C₆-cycloalkenyl: cyclobuten-1-yl, cyclobuten-3-yl, cyclopenten-1-yl,cyclopenten-3-yl, cyclopenten-4-yl, cyclohexen-1-yl, cyclohexen-3-yl andcyclohexen-4-yl;

heterocyclyl, and also the heterocyclyl radicals in heterocyclyloxy:three- to seven-membered saturated or partially unsaturated mono- orpolycyclic heterocycles which contain one to three hetero atoms selectedfrom a group consisting of oxygen, nitrogen and sulfur, such asoxiranyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl,3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl,4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl,4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl,4-pyrazolidinyl, 5-pyrazolidinyl, 2—oxazolidinyl, 4-Oxazolidinyl,5-Oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl,2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl,1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl,1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl,1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl,1,3,4-triazolidin-2-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl,2,3-dihydrofuran-4-yl, 2,3-dihydrofuran-5-yl, 2,5-dihydrofuran-2-yl,2,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl,2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl,2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl,2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl,2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl,2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl,4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl,4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl,2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl,2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl,2,3-dihydroisothiazol-5-yl, 4,5-dihydroisothiazol-3-yl,4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl,2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl,2,5-dihydroisothiazol-5-yl, 2,3-dihydropyrazol-3-yl,2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl,4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,5-dihydropyrazol-3-yl,2,5-dihydropyrazol-4-yl, 2,5-dihydropyrazol-5-yl,2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl,4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl,2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl,2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl,2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2-yl,4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl,2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl,2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl,2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl,4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl,4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl,2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2-morpholinyl,3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl,3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl,2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl,5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl,1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl,1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl,3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl,3-tetrahydrothiopyranyl, 4-tetrahydrothiopyranyl, 1,3-dioxolan-2-yl,3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl,4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl,2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl,1,3-dihydrooxazin-2-yl,

hetaryl, and also the hetaryl radicals in hetaryloxy:

aromatic mono- or polycyclic radicals which, besides carbon ringmembers, may additionally contain one to four nitrogen atoms or one tothree nitrogen atoms and one oxygen or one sulfur atom or one oxygen andone sulfur atom, eg. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl,3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-thiazolyl, 4-thiazolyl,5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl,1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl,1,2,4,5-tetrazin-3-yl, and also the corresponding benzo-fusedderivatives.

All phenyl, hetaryl and heterocyclyl rings are preferably unsubstitutedor carry one to three halogen atoms and/or one or two radicals selectedfrom the following group: nitro, cyano, methyl, trifluoromethyl,methoxy, trifluoromethoxy or methoxycarbonyl.

With a view to the use of the compounds of the formula I according tothe invention as herbicides, the variables preferably have the followingmeanings, viz. in each case alone or in combination:

R¹ is nitro, halogen, cyano, thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, —OR³ or—S(O)_(n)R³;

particularly preferably nitro, halogen such as, for example, fluorine,chlorine or bromine, C₁-C₆-haloalkyl, —OR³ or —SO₂R³;

R² is hydrogen, nitro, halogen, cyano, thiocyanato, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,—OR³ or —S(O)_(n)R³;

particularly preferably hydrogen, nitro, halogen such as, for example,fluorine, chlorine or bromine, C₁-C₆-alkyl, C₁-C₆-haloalkyl, —OR³ or—SO₂R³;

R ³ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl;

particularly preferably hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₂-C₃-alkenyl, C₂-C₃-alkynyl or phenyl; where the abovementioned alkylradicals may be partially or fully halogenated and/or may carry one tothree of the following groups:

hydroxyl, mercapto, amino, cyano, R³, —OR³, —SR³, —N(R³)₂, ═NOR³,—OCOR³, —SCOR³, —NR³COR³, —CO₂R³, —COSR³, —CON(R³)₂,C₁-C₄-alkyliminooxy, C₁-C₄-alkoxyamino, C₁-C₄-alkylcarbonyl,C₁-C₄-alkoxy-C₂-C₆-alkoxycarbonyl, C₁-C₄-alkylsulfonyl, heterocyclyl,heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy andhetaryloxy, where the eight last mentioned radicals may in turn besubstituted;

also preferred is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl; where the abovementionedalkyl radicals may be partially or fully halogenated and/or may carryone to three of the following groups:

hydroxyl, mercapto, amino, cyano, R³′, —OR³′, —SR³′, —N(R³′)₂, ═NOR³′,—OCOR³′, —SCOR³′, —NR³′—COR³′, CO₂R³′, —COSR³′, —CON(R³′)₂,C₁-C₄-alkyliminooxy, C₁-C₄-alkoxyamino, C₁-C₄-alkylcarbonyl,C₁-C₄-alkoxy-C₂-C₆-alkoxycarbonyl, C₁-C₄-alkylsulfonyl, heterocyclyl,heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy andhetaryloxy, where the eight last mentioned radicals may in turn besubstituted; (wherein R³′ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl);

n is 0, 1 or 2, particularly preferably 0 or 2;

X¹ is a straight-chain or branched C₁-C₄-alkylene, a C₂-C₄-alkenylene ora C₂-C₄-alkynylene chain, particularly preferably an ethylene,propylene, propenylene or propynylene chain which is interrupted by ahetero atom selected from the group consisting of

oxygen and sulfur, preferably oxygen,

where the abovementioned alkylene, alkenylene or alkynylene radicals maybe partially halogenated and/or may carry one to three of the followinggroups:

—OR⁴, —OCOR⁴, —OCONHR⁴ or —OSO₂R⁴;

R⁴ is hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; particularly preferablyhydrogen, methyl, ethyl or trifluoromethyl;

R⁵ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl,C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl,C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, where the alkyl radicals may in each case besubstituted by in each case one or more of the following radicals:

cyano, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino,C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy.

R⁶, R⁷, R⁹ and R¹¹ are each hydrogen or C₁-C₄-alkyl;

particularly preferably hydrogen, methyl or ethyl;

R⁸ is hydrogen, C₁-C₄-alkyl, C₃-C₄-cycloalkyl, where the two lastmentioned groups may carry one to three of the following substituents:halogen, C₁-C₄-alkoxy or C₁-C₄-alkylthio;

tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl,tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl,tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl,1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithian-2-yl or1,3-dithiolan-2-yl, where the six last mentioned groups may in each casecarry one to three C₁-C₄-alkyl radicals; particularly preferablyhydrogen, methyl, ethyl, cyclopropyl, di(methoxy)methyl,di(ethoxy)methyl, 2-ethylthiopropyl, tetrahydropyran-2-yl,tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl,tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl,1,3-dioxan-2-yl, 5,5-dimethyl-1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl,1,3-oxathian-2-yl, 1,3-dithiolan-2-yl, 5,5-dimethyl-1,3-dithian-2-yl or1-methylthiocyclopropyl;

R¹⁰ is hydrogen, C₁-C₄-alkyl or C₁-C₄-alkoxycarbonyl;

particularly preferably hydrogen, methyl or methoxycarbonyl.

Likewise, it may be advantageous for R⁸ and R¹¹ to form a π bond, thusgiving rise to a double bond system.

Alternatively, the CR⁸R⁹ unit may advantageously be replaced by C═O.

Particular preference is given to the compounds of the formula Ia, whereR¹ is attached in position 2 and R² is attached in position 4 of thephenyl ring.

Most particular preference is given to the compounds of the formula Iain which the substituents R¹, R² and Q are each as defined above, X¹ isa C₁-C₂-alkylene or a C₂-alkynylene chain containing one further oxygenand

Het is a three- to six-membered, preferably a five- or six-membered,partially or fully saturated heterocyclic group or a three- tosix-membered, preferably a five- or six-membered, heteroaromatic grouphaving up to three hetero atoms, particularly preferably having one ortwo hetero atoms selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

particularly preferably from the following two groups:

nitrogen or

oxygen in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may bepartially or fully halogenated and/or may be substituted by R⁵.

Furthermore, most particular preference is given to compounds of theformula Ia according to the invention in which the substituents R¹, R²and X¹ are each as defined above and Het is a five- or six-memberedpartially or fully saturated heterocyclic group or a five- orsix-membered heteroaromatic group having up to three hetero atoms,particularly preferably having one or two hetero atoms selected from thefollowing three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

particularly preferably from the following two groups:

nitrogen or

oxygen in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may bepartially or fully halogenated and/or may be substituted by R⁵.

Particular preference is given to the compounds Ib of Tables 1 to 36.

TABLE A No. X¹* Het 1 OCH₂ oxiranyl 2 OCH₂ 3-methyl-2-oxiranyl 3 OCH₂2-oxetanyl 4 OCH₂ 3-hydroxy-3-methyl-2-oxetanyl 5 OCH₂3-hydroxy-3-ethyl-2-oxetanyl 6 OCH₂ 3-hydroxy-3-propyl-2-oxetanyl 7 OCH₂3-hydroxy-3-butyl-2-oxetanyl 8 OCH₂ 3-methoxy-3-methyl-2-oxetanyl 9 OCH₂3-methoxy-3-ethyl-2-oxetanyl 10 OCH₂ 3-methoxy-3-propyl-2-oxetanyl 11OCH₂ 3-methoxy-3-butyl-2-oxetanyl 12 OCH₂ 3-trimethylsilyl-oxy-3-methyl-2-oxetanyl 13 OCH₂ 3-trimethylsilyl- oxy-3-ethyl-2-oxetanyl14 OCH₂ 3-trimethylsilyl- oxy-3-propyl-2-oxetanyl 15 OCH₂3-trimethylsilyl- oxy-3-butyl-2-oxetanyl 16 OCH₂ 3-oxetanyl 17 OCH₂2-furyl 18 OCH₂ 4,5-dihydro-2-furyl 19 OCH₂ 2,3-dihydro-2-furyl 20 OCH₂3-furyl 21 OCH₂ 4,5-dihydro-3-furyl 22 OCH₂ 2,3-dihydro-3-furyl 23 OCH₂2-thienyl 24 OCH₂ 4,5-dihydro-2-thienyl 25 OCH₂ 2,3-dihydro-2-thienyl 26OCH₂ 5-chloro-2-thienyl 27 OCH₂ 5-methyl-2-thienyl 28 OCH₂ 3-thienyl 29OCH₂ 4,5-dihydro-3-thienyl 30 OCH₂ 2,3-dihydro-3-thienyl 31 OCH₂2-pyrrolyl 32 OCH₂ 2,5-dihydro-2-pyrrolyl 33 OCH₂ 3-pyrrolyl 34 OCH₂2,5-dihydro-3-pyrrolyl 35 OCH₂ 3-isoxazolyl 36 OCH₂4-methyl-3-isoxazolyl 37 OCH₂ 5-methyl-3-isoxazolyl 38 OCH₂4,5-dimethyl-3-isoxazolyl 39 OCH₂ 4,5-dihydro-3-isoxazolyl 40 OCH₂4-methyl-4,5-dihydro-3-isoxazolyl 41 OCH₂5-methyl-4,5-dihydro-3-isoxazolyl 42 OCH₂ 4,5-dimethyl-4,5-di-hydro-3-isoxazolyl 43 OCH₂ 4-isoxazolyl 44 OCH₂ 3-methyl-4-isoxazolyl 45OCH₂ 5-methyl-4-isoxazolyl 46 OCH₂ 5-cyclopropyl-4-isoxazolyl 47 OCH₂5-phenyl-4-isoxazolyl 48 OCH₂ 3,5-dimethyl-4-isoxazolyl 49 OCH₂4,5-dihydro-4-isoxazolyl 50 OCH₂ 3-methyl-4,5-dihydro-4-isoxazolyl 51OCH₂ 5-methyl-4,5-dihydro-4-isoxazolyl 52 OCH₂ 3,5-dimethyl-4,5-di-hydro-4-isoxazolyl 53 OCH₂ 5-isoxazolyl 54 OCH₂ 3-methyl-5-isoxazolyl 55OCH₂ 4-methyl-5-isoxazolyl 56 OCH₂ 3,4-dimethyl-5-isoxazolyl 57 OCH₂4,5-dihydro-5-isoxazolyl 58 OCH₂ 3-methyl-4,5-dihydro-5-isoxazolyl 59OCH₂ 4-methyl-4,5-dihydro-5-isoxazolyl 60 OCH₂ 3,4-dimethyl-4,5-di-hydro-5-isoxazolyl 61 OCH₂ 3-isothiazolyl 62 OCH₂4-methyl-3-isothiazolyl 63 OCH₂ 5-methyl-3-isothiazolyl 64 OCH₂4-isothiazolyl 65 OCH₂ 3-methyl-4-isothiazolyl 66 OCH₂5-methyl-4-isothiazolyl 67 OCH₂ 5-isothiazolyl 68 OCH₂3-methyl-5-isothiazolyl 69 OCH₂ 4-methyl-5-isothiazolyl 70 OCH₂2-oxazolyl 71 OCH₂ 4-oxazolyl 72 OCH₂ 5-oxazolyl 73 OCH₂ 2-thiazolyl 74OCH₂ 4-thiazolyl 75 OCH₂ 5-thiazolyl 76 OCH₂ 3-pyrazolyl 77 OCH₂4-pyrazolyl 78 OCH₂ 1-methyl-3-pyrazolyl 79 OCH₂ 1-methyl-4-pyrazolyl 80OCH₂ 1-methyl-5-pyrazolyl 81 OCH₂ 2-imidazolyl 82 OCH₂1-methyl-2-imidazolyl 83 OCH₂ 5-methyl-[1,3,4]-2-oxadiazolyl 84 OCH₂5-methyl-[1,2,4]-3-oxadiazolyl 85 OCH₂ 5-methyl-[1,3,4]-2-thiadiazolyl86 OCH₂ 5-methyl-[1,2,4]-3-thiadiazolyl 87 OCH₂ [1,2,4]-3-triazolyl 88OCH₂ [1,2,3]-4-triazolyl 89 OCH₂ 2-pyridyl 90 OCH₂ 6-chloro-2-pyridyl 91OCH₂ 6-methoxy-2-pyridyl 92 OCH₂ 6-trifluoromethyl-2-pyridyl 93 OCH₂3-pyridyl 94 OCH₂ 2-chloro-3-pyridyl 95 OCH₂ 2-methoxy-3-pyridyl 96 OCH₂4-pyridyl 97 OCH₂ 2-chloro-4-pyridyl 98 OCH₂ 2-methoxy-4-pyridyl 99 OCH₂2-ethoxy-4-pyridyl 100 OCH₂ 2-methylthio-4-pyridyl 101 OCH₂2-trifluoromethyl-5-pyridyl 102 OCH₂ 2-pyrimidinyl 103 OCH₂3-pyrimidinyl 104 OCH₂ 4-pyrimidinyl 105 OCH₂ 2-pyrazinyl 106 OCH₂3-pyridazinyl 107 OCH₂ 4-pyridazinyl 108 OCH₂ 2-(2H-1,3-oxazinyl) 109OCH₂ 2-(6H-1,3-oxazinyl) 110 OCH₂ 4-(6H-1,3-oxazinyl) 111 OCH₂6-(6H-1,3-oxazinyl) 112 OCH₂ [1,3,5]-2-triazinyl 113 OCH₂[1,2,4]-3-triazinyl 114 OCH₂ [1,2,4]-5-triazinyl 115 OCH₂[1,2,4]-6-triazinyl 116 CH₂O oxiranyl 117 CH₂O 3-methyl-2-oxiranyl 118CH₂O 2-oxetanyl 119 CH₂O 3-hydroxy-3-methyl-2-oxetanyl 120 CH₂O3-hydroxy-3-ethyl-2-oxetanyl 121 CH₂O 3-hydroxy-3-propyl-2-oxetanyl 122CH₂O 3-hydroxy-3-butyl-2-oxetanyl 123 CH₂O 3-methoxy-3-methyl-2-oxetanyl124 CH₂O 3-methoxy-3-ethyl-2-oxetanyl 125 CH₂O3-methoxy-3-propyl-2-oxetanyl 126 CH₂O 3-methoxy-3-butyl-2-oxetanyl 127CH₂O 3-trimethylsilyl- oxy-3-methyl-2-oxetanyl 128 CH₂O3-trimethylsilyl- oxy-3-ethyl-2-oxetanyl 129 CH₂O 3-trimethylsilyl-oxy-3-propyl-2-oxetanyl 130 CH₂O 3-trimethylsilyl-oxy-3-butyl-2-oxetanyl 131 CH₂O 3-oxetanyl 132 CH₂O 2-furyl 133 CH₂O4,5-dihydro-2-furyl 134 CH₂O 2,3-dihydro-2-furyl 135 CH₂O 3-furyl 136CH₂O 4,5-dihydro-3-furyl 137 CH₂O 2,3-dihydro-3-furyl 138 CH₂O 2-thienyl139 CH₂O 4,5-dihydro-2-thienyl 140 CH₂O 2,3-dihydro-2-thienyl 141 CH₂O5-chloro-2-thienyl 142 CH₂O 5-methyl-2-thienyl 143 CH₂O 3-thienyl 144CH₂O 4,5-dihydro-3-thienyl 145 CH₂O 2,3-dihydro-3-thienyl 146 CH₂O2-pyrrolyl 147 CH₂O 2,5-dihydro-2-pyrrolyl 148 CH₂O 3-pyrrolyl 149 CH₂O2,5-dihydro-3-pyrrolyl 150 CH₂O 3-isoxazolyl 151 CH₂O4-methyl-3-isoxazolyl 152 CH₂O 5-methyl-3-isoxazolyl 153 CH₂O4,5-dimethyl-3-isoxazolyl 154 CH₂O 4,5-dihydro-3-isoxazolyl 155 CH₂O4-methyl-4,5-dihydro-3-isoxazolyl 156 CH₂O5-methyl-4,5-dihydro-3-isoxazolyl 157 CH₂O 4,5-dimethyl-4,5-di-hydro-3-isoxazolyl 158 CH₂O 4-isoxazolyl 159 CH₂O 3-methyl-4-isoxazolyl160 CH₂O 5-methyl-4-isoxazolyl 161 CH₂O 5-cyclopropyl-4-isoxazolyl 162CH₂O 5-phenyl-4-isoxazolyl 163 CH₂O 3,5-dimethyl-4-isoxazolyl 164 CH₂O4,5-dihydro-4-isoxazolyl 165 CH₂O 3-methyl-4,5-dihydro-4-isoxazolyl 166CH₂O 5-methyl-4,5-dihydro-4-isoxazolyl 167 CH₂O 3,5-dimethyl-4,5-di-hydro-4-isoxazolyl 168 CH₂O 5-isoxazolyl 169 CH₂O 3-methyl-5-isoxazolyl170 CH₂O 4-methyl-5-isoxazolyl 171 CH₂O 3,4-dimethyl-5-isoxazolyl 172CH₂O 4,5-dihydro-5-isoxazolyl 173 CH₂O 3-methyl-4,5-dihydro-5-isoxazolyl174 CH₂O 4-methyl-4,5-dihydro-5-isoxazolyl 175 CH₂O 3,4-dimethyl-4,5-di-hydro-5-isoxazolyl 176 CH₂O 3-isothiazolyl 177 CH₂O4-methyl-3-isothiazolyl 178 CH₂O 5-methyl-3-isothiazolyl 179 CH₂O4-isothiazolyl 180 CH₂O 3-methyl-4-isothiazolyl 181 CH₂O5-methyl-4-isothiazolyl 182 CH₂O 5-isothiazolyl 183 CH₂O3-methyl-5-isothiazolyl 184 CH₂O 4-methyl-5-isothiazolyl 185 CH₂O2-oxazolyl 186 CH₂O 4-oxazolyl 187 CH₂O 5-oxazolyl 188 CH₂O 2-thiazolyl189 CH₂O 4-thiazolyl 190 CH₂O 5-thiazolyl 191 CH₂O 3-pyrazolyl 192 CH₂O4-pyrazolyl 193 CH₂O 1-methyl-3-pyrazolyl 194 CH₂O 1-methyl-4-pyrazolyl195 CH₂O 1-methyl-5-pyrazolyl 196 CH₂O 2-imidazolyl 197 CH₂O1-methyl-2-imidazolyl 198 CH₂O 5-methyl-[1,3,4]-2-oxadiazolyl 199 CH₂O5-methyl-[1,2,4]-3-oxadiazolyl 200 CH₂O 5-methyl-[1,3,4]-2-thiadiazolyl201 CH₂O 5-methyl-[1,2,4]-3-thiadiazolyl 202 CH₂O [1,2,4]-3-triazolyl203 CH₂O [1,2,3]-4-triazolyl 204 CH₂O 2-pyridyl 205 CH₂O6-chloro-2-pyridyl 206 CH₂O 6-methoxy-2-pyridyl 207 CH₂O6-trifluoromethyl-2-pyridyl 208 CH₂O 3-pyridyl 209 CH₂O2-chloro-3-pyridyl 210 CH₂O 2-methoxy-3-pyridyl 211 CH₂O 4-pyridyl 212CH₂O 2-chloro-4-pyridyl 213 CH₂O 2-methoxy-4-pyridyl 214 CH₂O2-ethoxy-4-pyridyl 215 CH₂O 2-methylthio-4-pyridyl 216 CH₂O2-trifluoromethyl-5-pyridyl 217 CH₂O 2-pyrimidinyl 218 CH₂O3-pyrimidinyl 219 CH₂O 4-pyrimidinyl 220 CH₂O 2-pyrazinyl 221 CH₂O3-pyridazinyl 222 CH₂O 4-pyridazinyl 223 CH₂O 2-(2H-1,3-oxazinyl) 224CH₂O 2-(6H-1,3-oxazinyl) 225 CH₂O 4-(6H-1,3-oxazinyl) 226 CH₂O6-(6H-1,3-oxazinyl) 227 CH₂O [1,3,5]-2-triazinyl 228 CH₂O[1,2,4]-3-triazinyl 229 CH₂O [1,2,4]-5-triazinyl 230 CH₂O[1,2,4]-6-triazinyl 231 OCH₂CH₂ oxiranyl 232 OCH₂CH₂ 3-methyl-2-oxiranyl233 OCH₂CH₂ 2-oxetanyl 234 OCH₂CH₂ 3-hydroxy-3-methyl-2-oxetanyl 235OCH₂CH₂ 3-hydroxy-3-ethyl-2-oxetanyl 236 OCH₂CH₂3-hydroxy-3-propyl-2-oxetanyl 237 OCH₂CH₂ 3-hydroxy-3-butyl-2-oxetanyl238 OCH₂CH₂ 3-methoxy-3-methyl-2-oxetanyl 239 OCH₂CH₂3-methoxy-3-ethyl-2-oxetanyl 240 OCH₂CH₂ 3-methoxy-3-propyl-2-oxetanyl241 OCH₂CH₂ 3-methoxy-3-butyl-2-oxetanyl 242 OCH₂CH₂ 3-trimethylsilyl-oxy-3-methyl-2-oxetanyl 243 OCH₂CH₂ 3-trimethylsilyl-oxy-3-ethyl-2-oxetanyl 244 OCH₂CH₂ 3-trimethylsilyl-oxy-3-propyl-2-oxetanyl 245 OCH₂CH₂ 3-trimethylsilyl-oxy-3-butyl-2-oxetanyl 246 OCH₂CH₂ 3-oxetanyl 247 OCH₂CH₂ 2-furyl 248OCH₂CH₂ 4,5-dihydro-2-furyl 249 OCH₂CH₂ 2,3-dihydro-2-furyl 250 OCH₂CH₂3-furyl 251 OCH₂CH₂ 4,5-dihydro-3-furyl 252 OCH₂CH₂ 2,3-dihydro-3-furyl253 OCH₂CH₂ 2-thienyl 254 OCH₂CH₂ 4,5-dihydro-2-thienyl 255 OCH₂CH₂2,3-dihydro-2-thienyl 256 OCH₂CH₂ 5-chloro-2-thienyl 257 OCH₂CH₂5-methyl-2-thienyl 258 OCH₂CH₂ 3-thienyl 259 OCH₂CH₂4,5-dihydro-3-thienyl 260 OCH₂CH₂ 2,3-dihydro-3-thienyl 261 OCH₂CH₂2-pyrrolyl 262 OCH₂CH₂ 2,5-dihydro-2-pyrrolyl 263 OCH₂CH₂ 3-pyrrolyl 264OCH₂CH₂ 2,5-dihydro-3-pyrrolyl 265 OCH₂CH₂ 3-isoxazolyl 266 OCH₂CH₂4-methyl-3-isoxazolyl 267 OCH₂CH₂ 5-methyl-3-isoxazolyl 268 OCH₂CH₂4,5-dimethyl-3-isoxazolyl 269 OCH₂CH₂ 4,5-dihydro-3-isoxazolyl 270OCH₂CH₂ 4-methyl-4,5-dihydro-3-isoxazolyl 271 OCH₂CH₂5-methyl-4,5-dihydro-3-isoxazolyl 272 OCH₂CH₂ 4,5-dimethyl-4,5-di-hydro-3-isoxazolyl 273 OCH₂CH₂ 4-isoxazolyl 274 OCH₂CH₂3-methyl-4-isoxazolyl 275 OCH₂CH₂ 5-methyl-4-isoxazolyl 276 OCH₂CH₂5-cyclopropyl-4-isoxazolyl 277 OCH₂CH₂ 5-phenyl-4-isoxazolyl 278 OCH₂CH₂3,5-dimethyl-4-isoxazolyl 279 OCH₂CH₂ 4,5-dihydro-4-isoxazolyl 280OCH₂CH₂ 3-methyl-4,5-dihydro-4-isoxazolyl 281 OCH₂CH₂5-methyl-4,5-dihydro-4-isoxazolyl 282 OCH₂CH₂ 3,5-dimethyl-4,5-di-hydro-4-isoxazolyl 283 OCH₂CH₂ 5-isoxazolyl 284 OCH₂CH₂3-methyl-5-isoxazolyl 285 OCH₂CH₂ 4-methyl-5-isoxazolyl 286 OCH₂CH₂3,4-dimethyl-5-isoxazolyl 287 OCH₂CH₂ 4,5-dihydro-5-isoxazolyl 288OCH₂CH₂ 3-methyl-4,5-dihydro-5-isoxazolyl 289 OCH₂CH₂4-methyl-4,5-dihydro-5-isoxazolyl 290 OCH₂CH₂ 3,4-dimethyl-4,5-di-hydro-5-isoxazolyl 291 OCH₂CH₂ 3-isothiazolyl 292 OCH₂CH₂4-methyl-3-isothiazolyl 293 OCH₂CH₂ 5-methyl-3-isothiazolyl 294 OCH₂CH₂4-isothiazolyl 295 OCH₂CH₂ 3-methyl-4-isothiazolyl 296 OCH₂CH₂5-methyl-4-isothiazolyl 297 OCH₂CH₂ 5-isothiazolyl 298 OCH₂CH₂3-methyl-5-isothiazolyl 299 OCH₂CH₂ 4-methyl-5-isothiazolyl 300 OCH₂CH₂2-oxazolyl 301 OCH₂CH₂ 4-oxazolyl 302 OCH₂CH₂ 5-oxazolyl 303 OCH₂CH₂2-thiazolyl 304 OCH₂CH₂ 4-thiazolyl 305 OCH₂CH₂ 5-thiazolyl 306 OCH₂CH₂3-pyrazolyl 307 OCH₂CH₂ 4-pyrazolyl 308 OCH₂CH₂ 1-methyl-3-pyrazolyl 309OCH₂CH₂ 1-methyl-4-pyrazolyl 310 OCH₂CH₂ 1-methyl-5-pyrazolyl 311OCH₂CH₂ 2-imidazolyl 312 OCH₂CH₂ 1-methyl-2-imidazolyl 313 OCH₂CH₂5-methyl-[1,3,4]-2-oxadiazolyl 314 OCH₂CH₂5-methyl-[1,2,4]-3-oxadiazolyl 315 OCH₂CH₂5-methyl-[1,3,4]-2-thiadiazolyl 316 OCH₂CH₂5-methyl-[1,2,4]-3-thiadiazolyl 317 OCH₂CH₂ [1,2,4]-3-triazolyl 318OCH₂CH₂ [1,2,3]-4-triazolyl 319 OCH₂CH₂ 2-pyridyl 320 OCH₂CH₂6-chloro-2-pyridyl 321 OCH₂CH₂ 6-methoxy-2-pyridyl 322 OCH₂CH₂6-trifluoromethyl-2-pyridyl 323 OCH₂CH₂ 3-pyridyl 324 OCH₂CH₂2-chloro-3-pyridyl 325 OCH₂CH₂ 2-methoxy-3-pyridyl 326 OCH₂CH₂ 4-pyridyl327 OCH₂CH₂ 2-chloro-4-pyridyl 328 OCH₂CH₂ 2-methoxy-4-pyridyl 329OCH₂CH₂ 2-ethoxy-4-pyridyl 330 OCH₂CH₂ 2-methylthio-4-pyridyl 331OCH₂CH₂ 2-trifluoromethyl-5-pyridyl 332 OCH₂CH₂ 2-pyrimidinyl 333OCH₂CH₂ 3-pyrimidinyl 334 OCH₂CH₂ 4-pyrimidinyl 335 OCH₂CH₂ 2-pyrazinyl336 OCH₂CH₂ 3-pyridazinyl 337 OCH₂CH₂ 4-pyridazinyl 338 OCH₂CH₂2-(2H-1,3-oxazinyl) 339 OCH₂CH₂ 2-(6H-1,3-oxazinyl) 340 OCH₂CH₂4-(6H-1,3-oxazinyl) 341 OCH₂CH₂ 6-(6H-1,3-oxazinyl) 342 OCH₂CH₂[1,3,5]-2-triazinyl 343 OCH₂CH₂ [1,2,4]-3-triazinyl 344 OCH₂CH₂[1,2,4]-5-triazinyl 345 OCH₂CH₂ [1,2,4]-6-triazinyl 346 CH₂CH₂O oxiranyl347 CH₂CH₂O 3-methyl-2-oxiranyl 348 CH₂CH₂O 2-oxetanyl 349 CH₂CH₂O3-hydroxy-3-methyl-2-oxetanyl 350 CH₂CH₂O 3-hydroxy-3-ethyl-2-oxetanyl351 CH₂CH₂O 3-hydroxy-3-propyl-2-oxetanyl 352 CH₂CH₂O3-hydroxy-3-butyl-2-oxetanyl 353 CH₂CH₂O 3-methoxy-3-methyl-2-oxetanyl354 CH₂CH₂O 3-methoxy-3-ethyl-2-oxetanyl 355 CH₂CH₂O3-methoxy-3-propyl-2-oxetanyl 356 CH₂CH₂O 3-methoxy-3-butyl-2-oxetanyl357 CH₂CH₂O 3-trimethylsilyl- oxy-3-methyl-2-oxetanyl 358 CH₂CH₂O3-trimethylsilyl- oxy-3-ethyl-2-oxetanyl 359 CH₂CH₂O 3-trimethylsilyl-oxy-3-propyl-2-oxetanyl 360 CH₂CH₂O 3-trimethylsilyl-oxy-3-butyl-2-oxetanyl 361 CH_(2CH) ₂O 3-oxetanyl 362 CH₂CH₂O 2-furyl363 CH₂CH₂O 4,5-dihydro-2-furyl 364 CH₂CH₂O 2,3-dihydro-2-furyl 365CH₂CH₂O 3-furyl 366 CH₂CH₂O 4,5-dihydro-3-furyl 367 CH₂CH₂O2,3-dihydro-3-furyl 368 CH₂CH₂O 2-thienyl 369 CH₂CH₂O4,5-dihydro-2-thienyl 370 CH₂CH₂O 2,3-dihydro-2-thienyl 371 CH₂CH₂O5-chloro-2-thienyl 372 CH₂CH₂O 5-methyl-2-thienyl 373 CH₂CH₂O 3-thienyl374 CH₂CH₂O 4,5-dihydro-3-thienyl 375 CH₂CH₂O 2,3-dihydro-3-thienyl 376CH₂CH₂O 2-pyrrolyl 377 CH₂CH₂O 2,5-dihydro-2-pyrrolyl 378 CH₂CH₂O3-pyrrolyl 379 CH₂CH₂O 2,5-dihydro-3-pyrrolyl 380 CH₂CH₂O 3-isoxazolyl381 CH₂CH₂O 4-methyl-3-isoxazolyl 382 CH₂CH₂O 5-methyl-3-isoxazolyl 383CH₂CH₂O 4,5-dimethyl-3-isoxazolyl 384 CH₂CH₂O 4,5-dihydro-3-isoxazolyl385 CH₂CH₂O 4-methyl-4,5-dihydro-3-isoxazolyl 386 CH₂CH₂O5-methyl-4,5-dihydro-3-isoxazolyl 387 CH₂CH₂O 4,5-dimethyl-4,5-di-hydro-3-isoxazolyl 388 CH₂CH₂O 4-isoxazolyl 389 CH₂CH₂O3-methyl-4-isoxazolyl 390 CH₂CH₂O 5-methyl-4-isoxazolyl 391 CH₂CH₂O5-cyclopropyl-4-isoxazolyl 392 CH₂CH₂O 5-phenyl-4-isoxazolyl 393 CH₂CH₂O3,5-dimethyl-4-isoxazolyl 394 CH₂CH₂O 4,5-dihydro-4-isoxazolyl 395CH₂CH₂O 3-methyl-4,5-dihydro-4-isoxazolyl 396 CH₂CH₂O5-methyl-4,5-dihydro-4-isoxazolyl 397 CH₂CH₂O 3,5-dimethyl-4,5-di-hydro-4-isoxazolyl 398 CH₂CH₂O 5-isoxazolyl 399 CH₂CH₂O3-methyl-5-isoxazolyl 400 CH₂CH₂O 4-methyl-5-isoxazolyl 401 CH₂CH₂O3,4-dimethyl-5-isoxazolyl 402 CH₂CH₂O 4,5-dihydro-5-isoxazolyl 403CH₂CH₂O 3-methyl-4,5-dihydro-5-isoxazolyl 404 CH₂CH₂O4-methyl-4,5-dihydro-5-isoxazolyl 405 CH₂CH₂O 3,4-dimethyl-4,5-di-hydro-5-isoxazolyl 406 CH₂CH₂O 3-isothiazolyl 407 CH₂CH₂O4-methyl-3-isothiazolyl 408 CH₂CH₂O 5-methyl-3-isothiazolyl 409 CH₂CH₂O4-isothiazolyl 410 CH₂CH₂O 3-methyl-4-isothiazolyl 411 CH₂CH₂O5-methyl-4-isothiazolyl 412 CH₂CH₂O 5-isothiazolyl 413 CH₂CH₂O3-methyl-5-isothiazolyl 414 CH₂CH₂O 4-methyl-5-isothiazolyl 415 CH₂CH₂O2-oxazolyl 416 CH₂CH₂O 4-oxazolyl 417 CH₂CH₂O 5-oxazolyl 418 CH₂CH₂O2-thiazolyl 419 CH₂CH₂O 4-thiazolyl 420 CH₂CH₂O 5-thiazolyl 421 CH₂CH₂O3-pyrazolyl 422 CH₂CH₂O 4-pyrazolyl 423 CH₂CH₂O 1-methyl-3-pyrazolyl 424CH₂CH₂O 1-methyl-4-pyrazolyl 425 CH₂CH₂O 1-methyl-5-pyrazolyl 426CH₂CH₂O 2-imidazolyl 427 CH₂CH₂O 1-methyl-2-imidazolyl 428 CH₂CH₂O5-methyl-[1,3,4]-2-oxadiazolyl 429 CH₂CH₂O5-methyl-[1,2,4]-3-oxadiazolyl 430 CH₂CH₂O5-methyl-[1,3,4]-2-thiadiazolyl 431 CH₂CH₂O5-methyl-[1,2,4]-3-thiadiazolyl 432 CH₂CH₂O [1,2,4]-3-triazolyl 433CH₂CH₂O [1,2,3]-4-triazolyl 434 CH₂CH₂O 2-pyridyl 435 CH₂CH₂O6-chloro-2-pyridyl 436 CH₂CH₂O 6-methoxy-2-pyridyl 437 CH₂CH₂O6-trifluoromethyl-2-pyridyl 438 CH₂CH₂O 3-pyridyl 439 CH₂CH₂O2-chloro-3-pyridyl 440 CH₂CH₂O 2-methoxy-3-pyridyl 441 CH₂CH₂O 4-pyridyl442 CH₂CH₂O 2-chloro-4-pyridyl 443 CH₂CH₂O 2-methoxy-4-pyridyl 444CH₂CH₂O 2-ethoxy-4-pyridyl 445 CH₂CH₂O 2-methylthio-4-pyridyl 446CH₂CH₂O 2-trifluoromethyl-5-pyridyl 447 CH₂CH₂O 2-pyrimidinyl 448CH₂CH₂O 3-pyrimidinyl 449 CH₂CH₂O 4-pyrimidinyl 450 CH₂CH₂O 2-pyrazinyl451 CH₂CH₂O 3-pyridazinyl 452 CH₂CH₂O 4-pyridazinyl 453 CH₂CH₂O2-(2H-1,3-oxazinyl) 454 CH₂CH₂O 2-(6H-1,3-oxazinyl) 455 CH₂CH₂O4-(6H-1,3-oxazinyl) 456 CH₂CH₂O 6-(6H-1,3-oxazinyl) 457 CH₂CH₂O[1,3,5]-2-triazinyl 458 CH₂CH₂O [1,2,4]-3-triazinyl 459 CH₂CH₂O[1,2,4]-5-triazinyl 460 CH₂CH₂O [1,2,4]-6-triazinyl 461 CH₂OCH₂ oxiranyl462 CH₂OCH₂ 3-methyl-2-oxiranyl 463 CH₂OCH₂ 2-oxetanyl 464 CH₂OCH₂3-hydroxy-3-methyl-2-oxetanyl 465 CH₂OCH₂ 3-hydroxy-3-ethyl-2-oxetanyl466 CH₂OCH₂ 3-hydroxy-3-propyl-2-oxetanyl 467 CH₂OCH₂3-hydroxy-3-butyl-2-oxetanyl 468 CH₂OCH₂ 3-methoxy-3-methyl-2-oxetanyl469 CH₂OCH₂ 3-methoxy-3-ethyl-2-oxetanyl 470 CH₂OCH₂3-methoxy-3-propyl-2-oxetanyl 471 CH₂OCH₂ 3-methoxy-3-butyl-2-oxetanyl472 CH₂OCH₂ 3-trimethylsilyl- oxy-3-methyl-2-oxetanyl 473 CH₂OCH₂3-trimethylsilyl- oxy-3-ethyl-2-oxetanyl 474 CH₂OCH₂ 3-trimethylsilyl-oxy-3-propyl-2-oxetanyl 475 CH₂OCH₂ 3-trimethylsilyl-oxy-3-butyl-2-oxetanyl 476 CH₂OCH₂ 3-oxetanyl 477 CH₂OCH₂ 2-furyl 478CH₂OCH₂ 4,5-dihydro-2-furyl 479 CH₂OCH₂ 2,3-dihydro-2-furyl 480 CH₂OCH₂3-furyl 481 CH₂OCH₂ 4,5-dihydro-3-furyl 482 CH₂OCH₂ 2,3-dihydro-3-furyl483 CH₂OCH₂ 2-thienyl 484 CH₂OCH₂ 4,5-dihydro-2-thienyl 485 CH₂OCH₂2,3-dihydro-2-thienyl 486 CH₂OCH₂ 5-chloro-2-thienyl 487 CH₂OCH₂5-methyl-2-thienyl 489 CH₂OCH₂ 4,5-dihydro-3-thienyl 490 CH₂OCH₂2,3-dihydro-3-thienyl 491 CH₂OCH₂ 2-pyrrolyl 492 CH₂OCH₂2,5-dihydro-3-pyrrolyl 493 CH₂OCH₂ 3-pyrrolyl 494 CH₂OCH₂2,5-dihydro-3-pyrrolyl 495 CH₂OCH₂ 3-isoxazolyl 496 CH₂OCH₂4-methyl-3-isoxazolyl 497 CH₂OCH₂ 5-methyl-3-isoxazolyl 498 CH₂OCH₂4,5-dimethyl-3-isoxazolyl 499 CH₂OCH₂ 4,5-dihydro-3-isoxazolyl 500CH₂OCH₂ 4-methyl-4,5-dihydro-3-isoxazolyl 501 CH₂OCH₂5-methyl-4,5-dihydro-3-isoxazolyl 502 CH₂OCH₂ 4,5-dimethyl-4,5-di-hydro-3-isoxazolyl 503 CH₂OCH₂ 4-isoxazolyl 504 CH₂OCH₂3-methyl-4-isoxazolyl 505 CH₂OCH₂ 5-methyl-4-isoxazolyl 506 CH₂OCH₂5-cyclopropyl-4-isoxazolyl 507 CH₂OCH₂ 5-phenyl-4-isoxazolyl 508 CH₂OCH₂3,5-dimethyl-4-isoxazolyl 509 CH₂OCH₂ 4,5-dihydro-4-isoxazolyl 510CH₂OCH₂ 3-methyl-4,5-dihydro-4-isoxazolyl 511 CH₂OCH₂5-methyl-4,5-dihydro-4-isoxazolyl 512 CH₂OCH₂ 3,5-dimethyl-4,5-di-hydro-4-isoxazolyl 513 CH₂OCH₂ 5-isoxazolyl 514 CH₂OCH₂3-methyl-5-isoxazolyl 515 CH₂OCH₂ 4-methyl-5-isoxazolyl 516 CH₂OCH₂3,4-dimethyl-5-isoxazolyl 517 CH₂OCH₂ 4,5-dihydro-5-isoxazolyl 518CH₂OCH₂ 3-methyl-4,5-dihydro-5-isoxazolyl 519 CH₂OCH₂4-methyl-4,5-dihydro-5-isoxazolyl 520 CH₂OCH₂ 3,4-dimethyl-4,5-di-hydro-5-isoxazolyl 521 CH₂OCH₂ 3-isothiazolyl 522 CH₂OCH₂4-methyl-3-isothiazolyl 523 CH₂OCH₂ 5-methyl-3-isothiazolyl 524 CH₂OCH₂4-isothiazolyl 525 CH₂OCH₂ 3-methyl-4-isothiazolyl 526 CH₂OCH₂5-methyl-4-isothiazolyl 527 CH₂OCH₂ 5-isothiazolyl 528 CH₂OCH₂3-methyl-5-isothiazolyl 529 CH₂OCH₂ 4-methyl-5-isothiazolyl 530 CH₂OCH₂2-oxazolyl 531 CH₂OCH₂ 4-oxazolyl 532 CH₂OCH₂ 5-oxazolyl 533 CH₂OCH₂2-thiazolyl 534 CH₂OCH₂ 4-thiazolyl 535 CH₂OCH₂ 5-thiazolyl 536 CH₂OCH₂3-pyrazolyl 537 CH₂OCH₂ 4-pyrazolyl 538 CH₂OCH₂ 1-methyl-3-pyrazolyl 539CH₂OCH₂ 1-methyl-4-pyrazolyl 540 CH₂OCH₂ 1-methyl-5-pyrazolyl 541CH₂OCH₂ 2-imidazolyl 542 CH₂OCH₂ 1-methyl-2-imidazolyl 543 CH₂OCH₂5-methyl-[1,3,4]-2-oxadiazolyl 544 CH₂OCH₂5-methyl-[1,2,4]-3-oxadiazolyl 545 CH₂OCH₂5-methyl-[1,3,4]-2-thiadiazolyl 546 CH₂OCH₂5-methyl-[1,2,4]-3-thiadiazolyl 547 CH₂OCH₂ [1,2,4]-3-triazolyl 548CH₂OCH₂ [1,2,3]-4-triazolyl 549 CH₂OCH₂ 2-pyridyl 550 CH₂OCH₂6-chloro-2-pyridyl 551 CH₂OCH₂ 6-methoxy-2-pyridyl 552 CH₂OCH₂6-trifluoromethyl-2-pyridyl 553 CH₂OCH₂ 3-pyridyl 554 CH₂OCH₂2-chloro-3-pyridyl 555 CH₂OCH₂ 2-methoxy-3-pyridyl 556 CH₂OCH₂ 4-pyridyl557 CH₂OCH₂ 2-chloro-4-pyridyl 558 CH₂OCH₂ 2-methoxy-4-pyridyl 559CH₂OCH₂ 2-ethoxy-4-pyridyl 560 CH₂OCH₂ 2-methylthio-4-pyridyl 561CH₂OCH₂ 2-trifluoromethyl-5-pyridyl 562 CH₂OCH₂ 2-pyrimidinyl 563CH₂OCH₂ 3-pyrimidinyl 564 CH₂OCH₂ 4-pyrimidinyl 565 CH₂OCH₂ 2-pyrazinyl566 CH₂OCH₂ 3-pyridazinyl 567 CH₂OCH₂ 4-pyridazinyl 568 CH₂OCH₂2-(2H-1,3-oxazinyl) 569 CH₂OCH₂ 2-(6H-1,3-oxazinyl) 570 CH₂OCH₂4-(6H-1,3-oxazinyl) 571 CH₂OCH₂ 6-(6H-1,3-oxazinyl) 572 CH₂OCH₂[1,3,5]-2-triazinyl 573 CH₂OCH₂ [1,2,4]-3-triazinyl 574 CH₂OCH₂[1,2,4]-5-triazinyl 575 CH₂OCH₂ [1,2,4]-6-triazinyl 576 CH₂OCH₂CH═CHoxiranyl 577 CH₂OCH₂CH═CH 3-methyl-2-oxiranyl 578 CH₂OCH₂CH═CH2-oxetanyl 579 CH₂OCH₂CH═CH 3-hydroxy-3-methyl-2-oxetanyl 580CH₂OCH₂CH═CH 3-hydroxy-3-ethyl-2-oxetanyl 581 CH₂OCH₂CH═CH3-hydroxy-3-propyl-2-oxetanyl 582 CH₂OCH₂CH═CH3-hydroxy-3-butyl-2-oxetanyl 583 CH₂OCH₂CH═CH3-methoxy-3-methyl-2-oxetanyl 584 CH₂OCH₂CH═CH3-methoxy-3-ethyl-2-oxetanyl 585 CH₂OCH₂CH═CH3-methoxy-3-propyl-2-oxetanyl 586 CH₂OCH₂CH═CH3-methoxy-3-butyl-2-oxetanyl 587 CH₂OCH₂CH═CH 3-trimethylsilyl-oxy-3-methyl-2-oxetanyl 588 CH₂OCH₂CH═CH 3-trimethylsilyl-oxy-3-ethyl-2-oxetanyl 589 CH₂OCH₂CH═CH 3-trimethylsilyl-oxy-3-propyl-2-oxetanyl 590 CH₂OCH₂CH═CH 3-trimethylsilyl-oxy-3-butyl-2-oxetanyl 591 CH₂OCH₂CH═CH 3-oxetanyl 592 CH₂OCH₂CH═CH2-furyl 593 CH₂OCH₂CH═CH 4,5-dihydro-2-furyl 594 CH₂OCH₂CH═CH2,3-dihydro-2-furyl 595 CH₂OCH₂CH═CH 3-furyl 596 CH₂OCH₂CH═CH4,5-dihydro-3-furyl 597 CH₂OCH₂CH═CH 2,3-dihydro-3-furyl 598CH₂OCH₂CH═CH 2-thienyl 599 CH₂OCH₂CH═CH 4,5-dihydro-2-thienyl 600CH₂OCH₂CH═CH 2,3-dihydro-2-thienyl 601 CH₂OCH₂CH═CH 5-chloro-2-thienyl602 CH₂OCH₂CH═CH 5-methyl-2-thienyl 603 CH₂OCH₂CH═CH 3-thienyl 604CH₂OCH₂CH═CH 4,5-dihydro-3-thienyl 605 CH₂OCH₂CH═CH2,3-dihydro-3-thienyl 606 CH₂OCH₂CH═CH 2-pyrrolyl 607 CH₂OCH₂CH═CH2,5-dihydro-2-pyrrolyl 608 CH₂OCH₂CH═CH 3-pyrrolyl 609 CH₂OCH₂CH═CH2,5-dihydro-3-pyrrolyl 610 CH₂OCH₂CH═CH 3-isoxazolyl 611 CH₂OCH₂CH═CH4-methyl-3-isoxazolyl 612 CH₂OCH₂CH═CH 5-methyl-3-isoxazolyl 613CH₂OCH₂CH═CH 4,5-dimethyl-3-isoxazolyl 614 CH₂OCH₂CH═CH4,5-dihydro-3-isoxazolyl 615 CH₂OCH₂CH═CH4-methyl-4,5-dihydro-3-isoxazolyl 616 CH₂OCH₂CH═CH5-methyl-4,5-dihydro-3-isoxazolyl 617 CH₂OCH₂CH═CH 4,5-dimethyl-4,5-di-hydro-3-isoxazolyl 618 CH₂OCH₂CH═CH 4-isoxazolyl 619 CH₂OCH₂CH═CH3-methyl-4-isoxazolyl 620 CH₂OCH₂CH═CH 5-methyl-4-isoxazolyl 621CH₂OCH₂CH═CH 5-cyclopropyl-4-isoxazolyl 622 CH₂OCH₂CH═CH5-phenyl-4-isoxazolyl 623 CH₂OCH₂CH═CH 3,5-dimethyl-4-isoxazolyl 624CH₂OCH₂CH═CH 4,5-dihydro-4-isoxazolyl 625 CH₂OCH₂CH═CH3-methyl-4,5-dihydro-4-isoxazolyl 626 CH₂OCH₂CH═CH5-methyl-4,5-dihydro-4-isoxazolyl 627 CH₂OCH₂CH═CH 3,5-dimethyl-4,5-di-hydro-4-isoxazolyl 628 CH₂OCH₂CH═CH 5-isoxazolyl 629 CH₂OCH₂CH═CH3-methyl-5-isoxazolyl 630 CH₂OCH₂CH═CH 4-methyl-5-isoxazolyl 631CH₂OCH₂CH═CH 3,4-dimethyl-5-isoxazolyl 632 CH₂OCH₂CH═CH4,5-dihydro-5-isoxazolyl 633 CH₂OCH₂CH═CH3-methyl-4,5-dihydro-5-isoxazolyl 634 CH₂OCH₂CH═CH4-methyl-4,5-dihydro-5-isoxazolyl 635 CH₂OCH₂CH═CH 3,4-dimethyl-4,5-di-hydro-5-isoxazolyl 636 CH₂OCH₂CH═CH 3-isothiazolyl 637 CH₂OCH₂CH═CH4-methyl-3-isothiazolyl 638 CH₂OCH₂CH═CH 5-methyl-3-isothiazolyl 639CH₂OCH₂CH═CH 4-isothiazolyl 640 CH₂OCH₂CH═CH 3-methyl-4-isothiazolyl 641CH₂OCH₂CH═CH 5-methyl-4-isothiazolyl 642 CH₂OCH₂CH═CH 5-isothiazolyl 643CH₂OCH₂CH═CH 3-methyl-5-isothiazolyl 644 CH₂OCH₂CH═CH4-methyl-5-isothiazolyl 645 CH₂OCH₂CH═CH 2-oxazolyl 646 CH₂OCH₂CH═CH4-oxazolyl 647 CH₂OCH₂CH═CH 5-oxazolyl 648 CH₂OCH₂CH═CH 2-thiazolyl 649CH₂OCH₂CH═CH 4-thiazolyl 650 CH₂OCH₂CH═CH 5-thiazolyl 651 CH₂OCH₂CH═CH3-pyrazolyl 652 CH₂OCH₂CH═CH 4-pyrazolyl 653 CH₂OCH₂CH═CH1-methyl-3-pyrazolyl 654 CH₂OCH₂CH═CH 1-methyl-4-pyrazolyl 655CH₂OCH₂CH═CH 1-methyl-5-pyrazolyl 656 CH₂OCH₂CH═CH 2-imidazolyl 657CH₂OCH₂CH═CH 1-methyl-2-imidazolyl 658 CH₂OCH₂CH═CH5-methyl-[1,3,4]-2-oxadiazolyl 659 CH₂OCH₂CH═CH5-methyl-[1,2,4]-3-oxadiazolyl 660 CH₂OCH₂CH═CH5-methyl-[1,3,4]-2-thiadiazolyl 661 CH₂OCH₂CH═CH5-methyl-[1,2,4]-3-thiadiazolyl 662 CH₂OCH₂CH═CH [1,2,4]-3-triazolyl 663CH₂OCH₂CH═CH [1,2,3]-4-triazolyl 664 CH₂OCH₂CH═CH 2-pyridyl 665CH₂OCH₂CH═CH 6-chloro-2-pyridyl 666 CH₂OCH₂CH═CH 6-methoxy-2-pyridyl 667CH₂OCH₂CH═CH 6-trifluoromethyl-2-pyridyl 668 CH₂OCH₂CH═CH 3-pyridyl 669CH₂OCH₂CH═CH 2-chloro-3-pyridyl 670 CH₂OCH₂CH═CH 2-methoxy-3-pyridyl 671CH₂OCH₂CH═CH 4-pyridyl 672 CH₂OCH₂CH═CH 2-chloro-4-pyridyl 673CH₂OCH₂CH═CH 2-methoxy-4-pyridyl 674 CH₂OCH₂CH═CH 2-ethoxy-4-pyridyl 675CH₂OCH₂CH═CH 2-methylthio-4-pyridyl 676 CH₂OCH₂CH═CH2-trifluoromethyl-5-pyridyl 677 CH₂OCH₂CH═CH 2-pyrimidinyl 678CH₂OCH₂CH═CH 3-pyrimidinyl 679 CH₂OCH₂CH═CH 4-pyrimidinyl 680CH₂OCH₂CH═CH 2-pyrazinyl 681 CH₂OCH₂CH═CH 3-pyridazinyl 682 CH₂OCH₂CH═CH4-pyridazinyl 683 CH₂OCH₂CH═CH 2-(2H-1,3-oxazinyl) 684 CH₂OCH₂CH═CH2-(6H-1,3-oxazinyl) 685 CH₂OCH₂CH═CH 4-(6H-1,3-oxazinyl) 686CH₂OCH₂CH═CH 6-(6H-1,3-oxazinyl) 687 CH₂OCH₂CH═CH [1,3,5]-2-triazinyl688 CH₂OCH₂CH═CH [1,2,4]-3-triazinyl 689 CH₂OCH₂CH═CH[1,2,4]-5-triazinyl 690 CH₂OCH₂CH═CH [1,2,4]-6-triazinyl 691 CH═CHCH₂Ooxiranyl 692 CH═CHCH₂O 3-methyl-2-oxiranyl 693 CH═CHCH₂O 2-oxetanyl 694CH═CHCH₂O 3-hydroxy-3-methyl-2-oxetanyl 695 CH═CHCH₂O3-hydroxy-3-ethyl-2-oxetanyl 696 CH═CHCH₂O 3-hydroxy-3-propyl-2-oxetanyl697 CH═CHCH₂O 3-hydroxy-3-butyl-2-oxetanyl 698 CH═CHCH₂O3-methoxy-3-methyl-2-oxetanyl 699 CH═CHCH₂O 3-methoxy-3-ethyl-2-oxetanyl700 CH═CHCH₂O 3-methoxy-3-propyl-2-oxetanyl 701 CH═CHCH₂O3-methoxy-3-butyl-2-oxetanyl 702 CH═CHCH₂O 3-trimethylsilyl-oxy-3-methyl-2-oxetanyl 703 CH═CHCH₂O 3-trimethylsilyl-oxy-3-ethyl-2-oxetanyl 704 CH═CHCH₂O 3-trimethylsilyl-oxy-3-propyl-2-oxetanyl 705 CH═CHCH₂O 3-trimethylsilyl-oxy-3-butyl-2-oxetanyl 706 CH═CHCH₂O 3-oxetanyl 707 CH═CHCH₂O 2-furyl708 CH═CHCH₂O 4,5-dihydro-2-furyl 709 CH═CHCH₂O 2,3-dihydro-2-furyl 710CH═CHCH₂O 3-furyl 711 CH═CHCH₂O 4,5-dihydro-3-furyl 712 CH═CHCH₂O2,3-dihydro-3-furyl 713 CH═CHCH₂O 2-thienyl 714 CH═CHCH₂O4,5-dihydro-2-thienyl 715 CH═CHCH₂O 2,3-dihydro-2-thienyl 716 CH═CHCH₂O5-chloro-2-thienyl 717 CH═CHCH₂O 5-methyl-2-thienyl 718 CH═CHCH₂O3-thienyl 719 CH═CHCH₂O 4,5-dihydro-3-thienyl 720 CH═CHCH₂O2,3-dihydro-3-thienyl 721 CH═CHCH₂O 2-pyrrolyl 722 CH═CHCH₂O2,5-dihydro-2-pyrrolyl 723 CH═CHCH₂O 3-pyrrolyl 724 CH═CHCH₂O2,5-dihydro-3-pyrrolyl 725 CH═CHCH₂O 3-isoxazolyl 726 CH═CHCH₂O4-methyl-3-isoxazolyl 727 CH═CHCH₂O 5-methyl-3-isoxazolyl 728 CH═CHCH₂O4,5-dimethyl-3-isoxazolyl 729 CH═CHCH₂O 4,5-dihydro-3-isoxazolyl 730CH═CHCH₂O 4-methyl-4,5-dihydro-3-isoxazolyl 731 CH═CHCH₂O5-methyl-4,5-dihydro-3-isoxazolyl 732 CH═CHCH₂O 4,5-dimethyl-4,5-di-hydro-3-isoxazolyl 733 CH═CHCH₂O 4-isoxazolyl 734 CH═CHCH₂O3-methyl-4-isoxazolyl 735 CH═CHCH₂O 5-methyl-4-isoxazolyl 736 CH═CHCH₂O5-cyclopropyl-4-isoxazolyl 737 CH═CHCH₂O 5-phenyl-4-isoxazolyl 738CH═CHCH₂O 3,5-dimethyl-4-isoxazolyl 739 CH═CHCH₂O4,5-dihydro-4-isoxazolyl 740 CH═CHCH₂O 3-methyl-4,5-dihydro-4-isoxazolyl741 CH═CHCH₂O 5-methyl-4,5-dihydro-4-isoxazolyl 742 CH═CHCH₂O3,5-dimethyl-4,5-di- hydro-4-isoxazolyl 743 CH═CHCH₂O 5-isoxazolyl 744CH═CHCH₂O 3-methyl-5-isoxazolyl 745 CH═CHCH₂O 4-methyl-5-isoxazolyl 746CH═CHCH₂O 3,4-dimethyl-5-isoxazolyl 747 CH═CHCH₂O4,5-dihydro-5-isoxazolyl 748 CH═CHCH₂O 3-methyl-4,5-dihydro-5-isoxazolyl749 CH═CHCH₂O 4-methyl-4,5-dihydro-5-isoxazolyl 750 CH═CHCH₂O3,4-dimethyl-4,5-di- hydro-5-isoxazolyl 751 CH═CHCH₂O 3-isothiazolyl 752CH═CHCH₂O 4-methyl-3-isothiazolyl 753 CH═CHCH₂O 5-methyl-3-isothiazolyl754 CH═CHCH₂O 4-isothiazolyl 755 CH═CHCH₂O 3-methyl-4-isothiazolyl 756CH═CHCH₂O 5-methyl-4-isothiazolyl 757 CH═CHCH₂O 5-isothiazolyl 758CH═CHCH₂O 3-methyl-5-isothiazolyl 759 CH═CHCH₂O 4-methyl-5-isothiazolyl760 CH═CHCH₂O 2-oxazolyl 761 CH═CHCH₂O 4-oxazolyl 762 CH═CHCH₂O5-oxazolyl 763 CH═CHCH₂O 2-thiazolyl 764 CH═CHCH₂O 4-thiazolyl 765CH═CHCH₂O 5-thiazolyl 766 CH═CHCH₂O 3-pyrazolyl 767 CH═CHCH₂O4-pyrazolyl 768 CH═CHCH₂O 1-methyl-3-pyrazolyl 769 CH═CHCH₂O1-methyl-4-pyrazolyl 770 CH═CHCH₂O 1-methyl-5-pyrazolyl 771 CH═CHCH₂O2-imidazolyl 772 CH═CHCH₂O 1-methyl-2-imidazolyl 773 CH═CHCH₂O5-methyl-[1,3,4]-2-oxadiazolyl 774 CH═CHCH₂O5-methyl-[1,2,4]-3-oxadiazolyl 775 CH═CHCH₂O5-methyl-[1,3,4]-2-thiadiazolyl 776 CH═CHCH₂O5-methyl-[1,2,4]-3-thiadiazolyl 777 CH═CHCH₂O [1,2,4]-3-triazolyl 778CH═CHCH₂O [1,2,3]-4-triazolyl 779 CH═CHCH₂O 2-pyridyl 780 CH═CHCH₂O6-chloro-2-pyridyl 781 CH═CHCH₂O 6-methoxy-2-pyridyl 782 CH═CHCH₂O6-trifluoromethyl-2-pyridyl 783 CH═CHCH₂O 3-pyridyl 784 CH═CHCH₂O2-chloro-3-pyridyl 785 CH═CHCH₂O 2-methoxy-3-pyridyl 786 CH═CHCH₂O4-pyridyl 787 CH═CHCH₂O 2-chloro-4-pyridyl 788 CH═CHCH₂O2-methoxy-4-pyridyl 789 CH═CHCH₂O 2-ethoxy-4-pyridyl 790 CH═CHCH₂O2-methylthio-4-pyridyl 791 CH═CHCH₂O 2-trifluoromethyl-5-pyridyl 792CH═CHCH₂O 2-pyrimidinyl 793 CH═CHCH₂O 3-pyrimidinyl 794 CH═CHCH₂O4-pyrimidinyl 795 CH═CHCH₂O 2-pyrazinyl 796 CH═CHCH₂O 3-pyridazinyl 797CH═CHCH₂O 4-pyridazinyl 798 CH═CHCH₂O 2-(2H-1,3-oxazinyl) 799 CH═CHCH₂O2-(6H-1,3-oxazinyl) 800 CH═CHCH₂O 4-(6H-1,3-oxazinyl) 801 CH═CHCH₂O6-(6H-1,3-oxazinyl) 802 CH═CHCH₂O [1,3,5]-2-triazinyl 803 CH═CHCH₂O[1,2,4]-3-triazinyl 804 CH═CHCH₂O [1,2,4]-5-triazinyl 805 CH═CHCH₂O[1,2,4]-6-triazinyl 806 C≡C—CH₂O oxiranyl 807 C≡C—CH₂O3-methyl-2-oxiranyl 808 C≡C—CH₂O 2-oxetanyl 809 C≡C—CH₂O3-hydroxy-3-methyl-2-oxetanyl 810 C≡C—CH₂O 3-hydroxy-3-ethyl-2-oxetanyl811 C≡C—CH₂O 3-hydroxy-3-propyl-2-oxetanyl 812 C≡C—CH₂O3-hydroxy-3-butyl-2-oxetanyl 813 C≡C—CH₂O 3-methoxy-3-methyl-2-oxetanyl814 C≡C—CH₂O 3-methoxy-3-ethyl-2-oxetanyl 815 C≡C—CH₂O3-methoxy-3-propyl-2-oxetanyl 816 C≡C—CH₂O 3-methoxy-3-butyl-2-oxetanyl817 C≡C—CH₂O 3-trimethylsilyl- oxy-3-methyl-2-oxetanyl 818 C≡C—CH₂O3-trimethylsilyl- oxy-3-ethyl-2-oxetanyl 819 C≡C—CH₂O 3-trimethylsilyl-oxy-3-propyl-2-oxetanyl 820 C≡C—CH₂O 3-trimethylsilyl-oxy-3-butyl-2-oxetanyl 821 C≡C—CH₂O 3-oxetanyl 822 C≡C—CH₂O 2-furyl 823C≡C—CH₂O 4,5-dihydro-2-furyl 824 C≡C—CH₂O 2,3-dihydro-2-furyl 825C≡C—CH₂O 3-furyl 826 C≡C—CH₂O 4,5-dihydro-3-furyl 827 C≡C—CH₂O2,3-dihydro-3-furyl 828 C≡C—CH₂O 2-thienyl 829 C≡C—CH₂O4,5-dihydro-2-thienyl 830 C≡C—CH₂O 2,3-dihydro-2-thienyl 831 C≡C—CH₂O5-chloro-2-thienyl 832 C≡C—CH₂O 5-methyl-2-thienyl 833 C≡C—CH₂O3-thienyl 834 C≡C—CH₂O 4,5-dihydro-3-thienyl 835 C≡C—CH₂O2,3-dihydro-3-thienyl 836 C≡C—CH₂O 2-pyrrolyl 837 C≡C—CH₂O2,5-dihydro-2-pyrrolyl 838 C≡C—CH₂O 3-pyrrolyl 839 C≡C—CH₂O2,5-dihydro-3-pyrrolyl 840 C≡C—CH₂O 3-isoxazolyl 841 C≡C—CH₂O4-methyl-3-isoxazolyl 842 C≡C—CH₂O 5-methyl-3-isoxazolyl 843 C≡C—CH₂O4,5-dimethyl-3-isoxazolyl 844 C≡C—CH₂O 4,5-dihydro-3-isoxazolyl 845C≡C—CH₂O 4-methyl-4,5-dihydro-3-isoxazolyl 846 C≡C—CH₂O5-methyl-4,5-dihydro-3-isoxazolyl 847 C≡C—CH₂O 4,5-dimethyl-4,5-di-hydro-3-isoxazolyl 848 C≡C—CH₂O 4-isoxazolyl 849 C≡C—CH₂O3-methyl-4-isoxazolyl 850 C≡C—CH₂O 5-methyl-4-isoxazolyl 851 C≡C—CH₂O5-cyclopropyl-4-isoxazolyl 852 C≡C—CH₂O 5-phenyl-4-isoxazolyl 853C≡C—CH₂O 3,5-dimethyl-4-isoxazolyl 854 C≡C—CH₂O 4,5-dihydro-4-isoxazolyl855 C≡C—CH₂O 3-methyl-4,5-dihydro-4-isoxazolyl 856 C≡C—CH₂O5-methyl-4,5-dihydro-4-isoxazolyl 857 C≡C—CH₂O 3,5-dimethyl-4,5-di-hydro-4-isoxazolyl 858 C≡C—CH₂O 5-isoxazolyl 859 C≡C—CH₂O3-methyl-5-isoxazolyl 860 C≡C—CH₂O 4-methyl-5-isoxazolyl 861 C≡C—CH₂O3,4-dimethyl-5-isoxazolyl 862 C≡C—CH₂O 4,5-dihydro-5-isoxazolyl 863C≡C—CH₂O 3-methyl-4,5-dihydro-5-isoxazolyl 864 C≡C—CH₂O4-methyl-4,5-dihydro-5-isoxazolyl 865 C≡C—CH₂O 3,4-dimethyl-4,5-di-hydro-5-isoxazolyl 866 C≡C—CH₂O 3-isothiazolyl 867 C≡C—CH₂O4-methyl-3-isothiazolyl 868 C≡C—CH₂O 5-methyl-3-isothiazolyl 869C≡C—CH₂O 4-isothiazolyl 870 C≡C—CH₂O 3-methyl-4-isothiazolyl 871C≡C—CH₂O 5-methyl-4-isothiazolyl 872 C≡C—CH₂O 5-isothiazolyl 873C≡C—CH₂O 3-methyl-5-isothiazolyl 874 C≡C—CH₂O 4-methyl-5-isothiazolyl875 C≡C—CH₂O 2-oxazolyl 876 C≡C—CH₂O 4-oxazolyl 877 C≡C—CH₂O 5-oxazolyl878 C≡C—CH₂O 2-thiazolyl 879 C≡C—CH₂O 4-thiazolyl 880 C≡C—CH₂O5-thiazolyl 881 C≡C—CH₂O 3-pyrazolyl 882 C≡C—CH₂O 4-pyrazolyl 883C≡C—CH₂O 1-methyl-3-pyrazolyl 884 C≡C—CH₂O 1-methyl-4-pyrazolyl 885C≡C—CH₂O 1-methyl-5-pyrazolyl 886 C≡C—CH₂O 2-imidazolyl 887 C≡C—CH₂O1-methyl-2-imidazolyl 888 C≡C—CH₂O 5-methyl-[1,3,4]-2-oxadiazolyl 889C≡C—CH₂O 5-methyl-[1,2,4]-3-oxadiazolyl 890 C≡C—CH₂O5-methyl-[1,3,4]-2-thiadiazolyl 891 C≡C—CH₂O5-methyl-[1,2,4]-3-thiadiazolyl 892 C≡C—CH₂O [1,2,4]-3-triazolyl 893C≡C—CH₂O [1,2,3]-4-triazolyl 894 C≡C—CH₂O 2-pyridyl 895 C≡C—CH₂O6-chloro-2-pyridyl 896 C≡C—CH₂O 6-methoxy-2-pyridyl 897 C≡C—CH₂O6-trifluoromethyl-2-pyridyl 898 C≡C—CH₂O 3-pyridyl 899 C≡C—CH₂O2-chloro-3-pyridyl 900 C≡C—CH₂O 2-methoxy-3-pyridyl 901 C≡C—CH₂O4-pyridyl 902 C≡C—CH₂O 2-chloro-4-pyridyl 903 C≡C—CH₂O2-methoxy-4-pyridyl 904 C≡C—CH₂O 2-ethoxy-4-pyridyl 905 C≡C—CH₂O2-methylthio-4-pyridyl 906 C≡C—CH₂O 2-trifluoromethyl-5-pyridyl 907C≡C—CH₂O 2-pyrimidinyl 908 C≡C—CH₂O 3-pyrimidinyl 909 C≡C—CH₂O4-pyrimidinyl 910 C≡C—CH₂O 2-pyrazinyl 911 C≡C—CH₂O 3-pyridazinyl 912C≡C—CH₂O 4-pyridazinyl 913 C≡C—CH₂O 2-(2H-1,3-oxazinyl) 914 C≡C—CH₂O2-(6H-1,3-oxazinyl) 915 C≡C—CH₂O 4-(6H-1,3-oxazinyl) 916 C≡C—CH₂O6-(6H-1,3-oxazinyl) 917 C≡C—CH₂O [1,3,5]-2-triazinyl 918 C≡C—CH₂O[1,2,4]-3-triazinyl 919 C≡C—CH₂O [1,2,4]-5-triazinyl 920 C≡C—CH₂O[1,2,4]-6-triazinyl *The bridge X¹ is connectect at the left end withthe central phenyl radical and at the right end with Het.

The Tables 1-36 below are based on the 2-benzoylcyclohexane-1,3-dionesof the formula Ib:

Table 1: Compounds 1.1-1.920

Compounds of the formula Ib, where R¹ is chlorine, R² is methylsulfonyl,R⁶, R⁷, R⁸, R⁹, R¹⁰ and R¹¹ are each hydrogen and where for eachindividual compound the substituents X¹ and Het correspond to one lineof Table A.

Table 2: Compounds 2.1-2.920

Compounds of the formula Ib, where R¹ and R² are each chlorine, R⁶, R⁷,R^(8,) R⁹, R¹⁰ and R¹¹ are each hydrogen and where for each individualcompounds the substituents X¹ and Het corresponds to one line of TableA.

Table 3: Compounds 3.1-3.920

Compounds of the formula Ib, where R¹ is chlorine, R² istrifluoromethyl, R⁶, R⁷, R⁸, R⁹, R¹⁰ and R¹¹ are each hydrogen and wherefor each individual compound the substituents X¹ and Het correspond toone line of Table A.

Table 4: Compounds 4.1-4.920

Compounds of the formula Ib, where R¹ is methyl, R² is chlorine, R⁶, R⁷,R⁸, R⁹, R¹⁰ and R¹¹ are each hydrogen and where for each individualcompound the substituents X¹ and Het correspond to one line of Table A.

Table 5: Compounds 5.1-5.920

Compounds of the formula Ib, where R¹ is methyl, R² is methylsulfonyl,R⁶, R⁷, R⁸, R⁹, R¹⁰ and R¹¹ are each hydrogen and where for eachindividual compound the substituents X¹ and Het correspond to one lineof Table A.

Table 6: Compounds 6.1-6.920

Compounds of the formula Ib, where R¹ is methyl, R² is trifluoromethyl,R⁶, R⁷, R⁸, R⁹, R¹⁰ and R¹¹ are each hydrogen and where for eachindividual compound the substituents X¹ and Het correspond to one lineof Table A.

Table 7: Compounds 7.1-7.920

Compounds of the formula Ib, where R¹ is chlorine, R² is methylsulfonyl,R⁶, R⁷, R¹⁰ and R¹¹ are each hydrogen, R⁸ and R⁹ are each methyl andwhere for each individual compound the substituents X¹ and Hetcorrespond to one line of Table A.

Table 8: Compounds 8.1-8.920

Compounds of the formula Ib, where R¹ and R² are each chlorine, R⁶, R⁷,R¹⁰ and R¹¹ are each hydrogen, R⁸ and R⁹ are each methyl and where foreach individual compound the substituents X¹ and Het correspond to oneline of Table A.

Table 9: Compounds 9.1-9.920

Compounds of the formula Ib, where R¹ is chlorine, R² istrifluoromethyl, R⁶ R⁷, R¹⁰ and R¹¹ are each hydrogen, R⁸ and R⁹ areeach methyl and where for each individual compound the substituents X¹and Het correspond to one line of Table A.

Table 10: Compounds 10.1-10.920

Compounds of the formula Ib, where R¹ is methyl, R² is chlorine, R⁶, R⁷,R¹⁰ and R¹¹ are each hydrogen, R⁸ and R⁹ are each methyl and where foreach individual compound the substituents X¹ and Het correspond to oneline of Table A.

Table 11: Compounds 11.1-11.920

Compounds of the formula Ib, where R¹ is methyl, R² is methylsulfonyl,R⁶, R⁷, R¹⁰ and R¹¹ are each hydrogen, R⁸ and R⁹ are each methyl andwhere for each individual compound the substituents X¹ and Hetcorrespond to one line of Table A.

Table 12: Compounds 12.1-12.920

Compounds of the formula Ib, where R¹ is methyl, R² is trifluoromethyl,R⁶, R⁷, R¹⁰ and R¹¹ are each hydrogen, R⁸ and R⁹ is methyl and where foreach individual compound the substituents X¹ and Het correspond to oneline of Table A.

Table 13: Compounds 13.1-13.920

Compounds of the formula Ib, where R¹ is chlorine, R² is methylsulfonyl,R⁶, R⁷, R⁸ and R⁹ are each hydrogen, R¹⁰ and R¹¹ are each methyl andwhere for each individual compound the substituents X¹ and Hetcorrespond to one line of Table A.

Table 14: Compounds 14.1-14.920

Compounds of the formula Ib, where R¹ and R2 is chlorine, R⁶, R⁷, R⁸ andR⁹ are each hydrogen, R¹⁰ and R¹¹ are each methyl and where for eachindividual compound the substituents X¹ and Het correspond to one lineof Table A.

Table 15: Compounds 15.1-15.920

Compounds of the formula Ib, where R¹ is chlorine, R² istrifluoromethyl, R⁶, R⁷, R⁸ and R⁹ are each hydrogen, R¹⁰ and R¹¹ areeach methyl and where for each individual compound the substituents X¹and Het correspond to one line of Table A.

Table 16: Compounds 16.1-16.920

Compounds of the formula Ib, where R¹ is methyl, R² is chlorine, R⁶, R⁷,R⁸ and R⁹ are each hydrogen, R¹⁰ and R¹¹ are each methyl and where foreach individual compound the substituents X¹ and Het correspond to oneline of Table A.

Table 17: Compounds 17.1-17.920

Compounds of the formula Ib, where R¹ is methyl, R² is methylsulfonyl,R⁶, R⁷, R⁸ and R⁹ are each hydrogen, R¹⁰ and R¹¹ are each methyl andwhere for each individual compound the substituents X¹ and Hetcorrespond to one line of Table A.

Table 18: Compounds 18.1-18.920

Compounds of the formula Ib, where R¹ is methyl, R² is trifluoromethyl,R⁶, R⁷, R⁸ and R⁹ are each hydrogen, R¹⁰ and R¹¹ are each methyl andwhere for each individual compound the substituents X¹ and Hetcorrespond to one line of Table A.

Table 19: Compounds 19.1-19.920

Compounds of the formula Ib, where R¹ is chlorine, R² is methylsulfonyl,R⁶, R⁷, R¹⁰ and R¹¹ are each methyl, the CR⁸R⁹ unit forms a group C═Oand where for each individual compound the substituents X¹ and Hetcorrespond to one line of Table A.

Table 20: Compounds 20.1-20.920

Compounds of the formula Ib, where R¹ and R² are each chlorine, R⁶, R⁷,R¹⁰ and R¹¹ are each methyl, the CR⁸R⁹ unit forms a group C═O and wherefor each individual compound the substituents X¹ and Het correspond toone line of Table A.

Table 21: Compounds 21.1-21.920

Compounds of the formula Ib, where R¹ is chlorine, R² istrifluoromethyl, R⁶, R⁷, R¹⁰ and R¹¹ are each methyl, the CR⁸R⁹ unitforms a group C═O and where for each individual compound thesubstituents X¹ and Het correspond to one line of Table A.

Table 22: Compounds 22.1-22.920

Compounds of the formula Ib, where R¹ is methyl, R² is chlorine, R⁶, R⁷,R¹⁰ and R¹¹ are each methyl, the CR⁸R⁹ unit forms a group C═O and wherefor each individual compound the substituents X¹ and Het correspond toone line of Table A.

Table 23: Compounds 23.1-23.920

Compounds of the formula Ib, where R¹ is methyl, R² is methylsulfonyl,R⁶, R⁷, R¹⁰ and R¹¹ are each methyl, the CR⁸R⁹ unit forms a group C═Oand where for each individual compound the substituents X¹ and Hetcorrespond to one line of Table A.

Table 24: Compounds 24.1-24.920

Compounds of the formula Ib, where R¹ is methyl, R² is trifluoromethyl,R⁶, R⁷, R¹⁰ and R¹¹ are each methyl, the CR⁸R⁹ unit forms a group C═Oand where for each individual compound the substituents X¹ and Hetcorrespond to one line of Table A.

Table 25: Compounds 25.1-25.920

Compounds of the formula Ib, where R¹ is methylsulfonyl, R⁶, R⁷, R⁸, R¹⁰and R¹¹ are each hydrogen, R⁹ is methyl, where for each individualcompound the substituents X¹ and Het correspond to one line of Table A.

Table 26: Compounds 26.1-26.920

Compounds of the formula Ib, where R¹ and R² are each chlorine, R⁶, R⁷,R⁸, R¹⁰ and R¹¹ are each hydrogen, R⁹ is methyl and where for eachindividual compound the substituents X¹ and Het correspond to one lineof Table A.

Table 27: Compounds 27.1-27.920

Compounds of the formula Ib, where R¹ is chlorine, R² istrifluoromethyl, R⁶, R⁷, R⁸, R¹⁰ and R¹¹ are each hydrogen, R⁹ is methyland where for each individual compound the substituents X¹ and Hetcorrespond to one line of Table A.

Table 28: Compounds 28.1-28.920

Compounds of the formula Ib, where R¹ is methyl, R² is chlorine, R⁶, R⁷,R⁸, R¹⁰ and R¹¹ are each hydrogen, R⁹ is methyl and where for eachindividual compound the substituents X¹ and Het correspond to one lineof Table A.

Table 29: Compounds 29.1-29.920

Compounds of the formula Ib, where R¹ is methyl, R² is methylsulfonyl,R⁶, R⁷, R⁸, R¹⁰ and R¹¹ are each hydrogen, R⁹ is methyl and where foreach individual compound the substituents X¹ and Het correspond to oneline of Table A.

Table 30: Compounds 30.1-30.920

Compounds of the formula Ib, where R¹ is methyl, R² is trifluoromethyl,R⁶, R⁷, R⁸, R¹⁰ and R¹¹ are each hydrogen, R⁹ is methyl and where foreach individual compound the substituents X¹ and Het correspond to oneline of Table A.

Table 31: Compounds 31.1-31.920

Compounds of the formula Ib, where R¹ is chlorine, R² is methylsulfonyl,R⁶, R⁷, R⁹ and R¹⁰ are each hydrogen, R⁸ and R¹¹ together form amethylene group and where for each individual compound the substituentsX¹ and Het correspond to one line of Table A.

Table 32: Compounds 32.1-32.920

Compounds of the formula Ib, where R¹ and R² are each chlorine, R⁶, R⁷,R⁹ and R¹⁰ are each hydrogen, R⁸ and R¹¹ together form a methylene groupand where for each individual compound the substituents X¹ and Hetcorrespond to one line of Table A.

Table 33: Compounds 33.1-33.920

Compounds of the formula Ib, where R¹ is chlorine, R² istrifluoromethyl, R⁶, R⁷, R⁹ and R¹⁰ are each hydrogen, R⁸ and R¹¹together form a methylene group and where for each individual compoundthe substituents X¹ and Het correspond to one line of Table A.

Table 34: Compounds 34.1-34.920

Compounds of the formula Ib, where R¹ is methyl, R² is chlorine, R⁶, R⁷,R⁹ and R¹⁰ are each hydrogen, R⁸ and R¹¹ together form a methylene groupand where for each individual compound the substituents X¹ and Hetcorrespond to one line of Table A.

Table 35: Compounds 35.1-35.920

Compounds of the formula Ib, where R¹ is methyl, R² is methylsulfonyl,R⁶, R⁷, R⁹ and R¹⁰ are each hydrogen, R⁸ and R¹¹ together form amethylene group and where for each individual compound the substituentsX¹ and Het correspond to one line of Table A.

Table 36: Compounds 36.1-36.920

Compounds of the formula Ib, where R¹ is methyl, R² is trifluoromethyl,R⁶, R⁷, R⁹ and R¹⁰ are each hydrogen, R⁸ and R¹¹ together form amethylene group and where for each individual compound the substituentsX¹ and Het correspond to one line of Table A.

The compounds I and their agriculturally useful salts are suitable, bothin the form of isomer mixtures and in the form of the pure isomers, asherbicides. The herbicidal compositions comprising I control vegetationon non-crop areas very efficiently, especially at high rates ofapplication. They act against broadleaved weeds and grass weeds in cropssuch as wheat, rice, maize, soya and cotton without causing anysignificant damage to the crop plants. This effect is mainly observed atlow rates of application.

Depending on the application method used, the compounds I, or thecompositions comprising them, can additionally be employed in a furthernumber of crop plants for eliminating unwanted plants.

Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spec., Manihotesculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica),Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris,Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica,Pyrus communnis, Ribes sylvestre, Ricinus communis, Saccharumofficinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S.vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum,Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds I may also be used in crops which toleratethe action of herbicides owing to breeding, including geneticengineering methods.

The herbicidal compositions or the active compounds can be applied pre-or post-emergence. If the active compounds are less well tolerated bycertain crop plants, application techniques may be used in which theherbicidal compositions are sprayed, with the aid of the sprayingequipment, in such a way that they come into contact as little aspossible, if at all, with the leaves of the sensitive crop plants, whilethe active compounds reach the leaves of unwanted plants growingunderneath, or the bare soil surface (post-directed, lay-by).

The compounds I, or the herbicidal compositions comprising them, can beused for example in the form of ready-to-spray aqueous solutions,powders, suspensions, also highly concentrated aqueous, oily or othersuspensions or dispersions, emulsions, oil dispersions, pastes, dusts,materials for broadcasting, or granules, by means of spraying,atomizing, dusting, broadcasting or watering. The application formsdepend on the intended uses; in any case, they should guarantee a veryfine distribution of the active compounds according to the invention.

Essentially, suitable inert auxiliaries include: mineral oil fractionsof medium to high boiling point, such as kerosene and diesel oil,furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, eg. paraffins,tetrahydronaphthalene, alkylated naphthalenes and their derivatives,alkylated benzenes and their derivatives, alcohols such as methanol,ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone, strongly polar solvents, eg. amines such asN-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thesubstituted 2-benzoylcyclohexane-1,3-diones, either as such or dissolvedin an oil or solvent, can be homogenized in water by means of a wettingagent, tackifier, dispersant or emulsifier. Alternatively, it ispossible to prepare concentrates comprising active compound, wettingagent, tackifier, dispersant or emulsifier and, if desired, solvent oroil, which are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metalsalts and ammonium salts of aromatic sulfonic acids, eg. ligno-,phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fattyacids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ethersulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta-and octadecanols, and also of fatty alcohol glycol ethers, condensatesof sulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene or of the naphthalenesulfonic acids withphenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol/ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, laurylalcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite wasteliquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixingor grinding the active compounds together with a solid carrier.

Granules, eg. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active compounds to solidcarriers. Solid carriers are mineral earths, such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the active compounds I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise from 0.001 to 98% by weight, preferably 0.01 to95% by weight of at least one active compound. The active compounds areemployed in a purity of from 90% to 100%, preferably 95% to 100%(according to the NMR spectrum).

The compounds I according to the invention can be formulated for exampleas follows:

I 20 parts by weight of the compound I are dissolved in a mixturecomposed of 80 parts by weight of alkylated benzene, 10 parts by weightof the adduct of 8 to 10 mol of ethylene oxide with 1 mol of oleic acidN-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonateand 5 parts by weight of the adduct of 40 mol of ethylene oxide with 1mol of castor oil. Pouring the solution into 100,000 parts by weight ofwater and finely distributing it therein gives an aqueous dispersionwhich comprises 0.02% by weight of the active compound.

II 20 parts by weight of the compound I are dissolved in a mixturecomposed of 40 parts by weight of cyclohexanone, 30 parts by weight ofisobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxidewith 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40mol of ethylene oxide with 1 mol of castor oil. Pouring the solutioninto 100,000 parts by weight of water and finely distributing it thereingives an aqueous dispersion which comprises 0.02% by weight of theactive compound.

III 20 parts by weight of the compound I are dissolved in a mixturecomposed of 25 parts by weight of cyclohexanone, 65 parts by weight of amineral oil fraction of boiling point 210 to 280° C. and 10 parts byweight of the adduct of 40 mol of ethylene oxide with 1 mol of castoroil. Pouring the solution into 100,000 parts by weight of water andfinely distributing it therein gives an aqueous dispersion whichcomprises 0.02% by weight of the active compound.

IV 20 parts by weight of the compound I are mixed thoroughly with 3parts by weight of sodium diisobutylnaphthalenesulfonate, 17 parts byweight of the sodium salt of a lignosulfonic acid from a sulfite wasteliquor and 60 parts by weight of pulverulent silica gel, and the mixtureis ground in a hammer mill. Finely distributing the mixture in 20,000parts by weight of water gives a spray mixture which comprises 0.1% byweight of the active compound.

V 3 parts by weight of the compound I are mixed with 97 parts by weightof finely divided kaolin. This gives a dust which comprises 3% by weightof the active compound.

VI 20 parts by weight of the compound I are mixed intimately with 2parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight offatty alcohol polyglycol ether, 2 parts by weight of the sodium salt ofa phenol/urea/formaldehyde condensate and 68 parts by weight of aparaffinic mineral oil. This gives a stable oily dispersion.

VII 1 part by weight of the compound I is dissolved in a mixturecomposed of 70 parts by weight of cyclohexanone, 20 parts by weight ofethoxylated isooctylphenol and 10 parts by weight of ethoxylated castoroil. This gives a stable emulsion concentrate.

VIII 1 part by weight of the compound I is dissolved in a mixturecomposed of 80 parts by weight of cyclohexanone and 20 parts by weightof Wettol® EM 31 (nonionic emulsifier based on ethoxylated castor oil).This gives a stable emulsion concentrate.

To widen the activity spectrum and to achieve synergistic effects, thesubstituted 2-benzoylcyclohexane-1,3-diones I may be mixed with a largenumber of representatives of other herbicidal or growth-regulatingactive compound groups and then applied concomitantly. Suitablecomponents for mixtures are, for example, 1,2,4-thiadiazoles,1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives,aminotriazoles, anilides, (het)aryloxyalkanoic acids and theirderivatives, benzoic acid and its derivatives, benzothiadiazinones,2-aroyl-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid andits derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, bipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, phenylpropionic acid andits derivatives, pyrazoles, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds I, alone orelse concomitantly in combination with other herbicides, in the form ofa mixture with other crop protection agents, for example together withagents for controlling pests or phytopathogenic fungi or bacteria. Alsoof interest is the miscibility with mineral salt solutions, which areemployed for treating nutritional and trace element deficiencies.Non-phytotoxic oils and oil concentrates may also be added.

The active compound application rates are from 0.001 to 3.0, preferably0.01 to 1.0 kg/ha of active substance (a.s.), depending on the controltarget, the season, the target plants and the growth stage.

The syntheses of some starting materials and products are describedbelow.

{2-chloro-3-[(1-methylpyrazol-5-yl)oxymethyl]-4-methyl-sulfonylphenyl}{5,5-dimethyl-1,3-dioxo-cyclohex-2-yl}methanone

step a: methyl 2-chloro-3-bromomethyl-4-methylsulfonylbenzoate

80 g (0.3 mol) of methyl 2-chloro-3-methyl-4-methylsulfonylbenzoate, 54g (0.31 mol) of N-bromosuccinimide and 1.5 g of azoisobutyronitrile arestirred at 76° C. for 6 h. The reaction mixture is filtered and freedform the solvent under reduced pressure. Yield: 104 g; m.p. 83-85° C.

step b: methyl2-chloro-[(1-methylpyrazol-5-yl)oxymethyl]-4-methylsulfonylbenzoate

4.3 g (44 mmol) of 1-methyl-5-hydroxypyrazol, 9.1 g of potassiumcarbonate and 100 ml of tetrahydrofurane are heated at 65° C. for 1 h.15 g (44 mmol) of methyl 2-chloro-3-bromomethyl-4-methylsulfonylbenzoateand 150 ml of tetrahydrofurane are added to this mixture and heated at40° C. for 4 h. This mixture is stirred for 12 h, freed from the solventunder reduced pressure, taken up in ethyl acetate, washed with sodiumbicarbonate solution and water, dried and freed form the solvent. Thecrude product is purified over silica gel (eluent: cyclohexane/ethylacetate=1/1). Yield: 7.6 g; m.p. 70° C.

Step c: 2-chloro-[(1-methylpyrazol-5-yl)oxymethyl]-4-methylsulfonylbenzoic acid

6.95 g (19 mmol) of methyl2-chloro-[(1-methylpyrazol-5-yl)oxymethyl]-4-methylsulfonylbenzoate in amixture of 30 ml of tetrahydrofurane and 30 ml of water are treated atroom temperature with 0.93 g of lithium hydroxide for 12 h. The reactionmixture is adjusted to pH4 with 10% strength hydrochloric acid andextracted with methylene chloride. The organic phase is dried and freedfrom the solvent. Yield: 4.3 g; m.p. 197° C.

Step d:{2-chloro-3-[(1-methylpyrazol-5-yl)oxymethyl]-4-methylsulfonylphenyl}{5,5-dimethyl-1,3-dioxo-cyclohex-2-yl}methanone

1.0 g (2.9 mmol) of2-chloro-3-[(1-methylpyrazol-5-yl)oxymethyl]-4-methylsulfonyl benzoicacid, 0.4 g (2.9 mmol) of dimedone and 0.72 g ofN,N-dicyclohexylcarbodiimide in 50 ml of acetonitrile are heated at 40°C. for 4 h. After the reaction mixture has been stirred for 12 h at roomtemperature, 0.87 g of triethylamine and 0.57 g of trimethylsilylnitrileare added. Afterwards the reaction mixture is heated at 40° C. for 6 h,filtered, freed from the solvent under reduced pressure and the residueis purified over silica gel (eluent: toluene/tetrahydrofurane/aceticacid: 100/0/0→4/1/0.1). Yield: 0.25 g; m.p.82° C.

TABLE 37

¹H M.p. NMR No. R⁶ R⁷ R⁸ R⁹ R¹⁰ R¹¹ X¹ Het [° C.] [ppm] 37.1 H H CH₃ CH₃H H CH₂O 1-methylpyrazal-5-yl 82 37.2 H H CH₃ CH₃ H H CH₂O 3,5-dime- 76thyl-1-pyra- zolyl 37.3 H H CH₃ CH₃ H H CH₂O 4-chloro-1- 75 pyrazolyl37.4 H CH₃ H H H CH₃ CH₂O 3,5-dime- 74 thyl-1-pyra- zolyl 37.5 H CH₃ H HH CH₃ CH₂O 4-chloro-1- 79 pyrazolyl 37.6 CH₃ CH₃ C═O CH₃ CH₃ CH₂O3,5-dime- 137 thyl-1-pyra- zolyl 37.7 CH₃ CH₃ C═O CH₃ CH₃ CH₂O4-chloro-1- 95 pyrazolyl

USE EXAMPLES

The herbicidal activity of the substituted2-benzoylcyclohexane-1,3-diones of the formula I was demonstrated bygreenhouse experiments:

The culture containers used were plastic pots containing loamy sand withapproximately 3.0% of humus as the substrate. The seeds of the testplants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had beensuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtranslucent plastic hoods until the plants had rooted. This cover causeduniform germination of the test plants, unless this was adverselyaffected by the active compounds.

For the post-emergence treatment, the test plants were first grown to aheight of 3 to 15 cm, depending on the plant habit, and only thentreated with the active compounds which had been suspended or emulsifiedin water. The test plants were for this purpose either sown directly andgrown in the same containers, or they were first grown separately asseedlings and transplanted into the test containers a few days prior totreatment.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

The evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least theabove-ground parts, and 0 means no damage, or normal course of growth.

We claim:
 1. A 2-benzoylcyclohexane-1,3-dione of formula I:

where: R¹ and R² are each hydrogen, mercapto, nitro, halogen, cyano,thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl,C₂-C₆-alkynyl, —OR³, —OCOR³, —OSO₂R³, —S(O)_(n)R³, —SO₂OR³, —SO₂N(R³)₂,—NR³SO₂R³ or —NR³COR³; R³ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl; where theabovementioned alkyl radicals may be partially or fully halogenatedand/or may carry one to three of the following groups: hydroxyl,mercapto, amino, cyano; n is 0, 1 or 2; Q is a cyclohexane-1,3-dionering with or without substitution which is attached in position 2; X¹ isa straight-chain or branched C₁-C₆-alkylene, a C₂-C₆-alkenylene or aC₂-C₆-alkynylene chain which is interrupted by a hetero atom selectedfrom the group consisting of: oxygen or sulfur, where the abovementionedalkyl, alkenyl or alkynyl radicals may be partially halogenated and/ormay carry one to three of the following groups: —OR⁴, —OCOR⁴, —OCONHR⁴or —OSO₂R⁴; R⁴ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,phenyl, phenyl-C₁-C₆-alkyl, where the abovementioned alkyl, alkenyl oralkynyl radicals may be partially or fully halogenated and/or may besubstituted by one or more of the following radicals: hydroxyl,mercapto, amino, cyano, nitro, formyl, C₁-C₄-alkylamino,C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl,C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio,C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy; Het is a three- tosix-membered partially or fully saturated heterocyclic group or a three-to six-membered heteroaromatic group having up to three nitrogen ringmembers as hetero atoms, where the abovementioned heterocyclic orheteroaromatic group may be partially or fully halogenated and/or may besubstituted by R⁵; R⁵ is hydrogen, hydroxyl, mercapto, amino, cyano,nitro, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino,C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, where the alkyl radicals may in eachcase be substituted by in each case one or more of the followingradicals: cyano, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino,C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy; or an agriculturally useful saltthereof.
 2. The 2-benzoylcyclohexane-1,3-dione of formula I defined inclaim 1 wherein the cyclohexane-1,3-dione ring Q is of formula II

wherein R⁶, R⁷, R⁹ and R¹¹ are each hydrogen or C₁-C₄-alkyl; R⁸ ishydrogen, C₁-C₄-alkyl or C₃-C₄-cycloalkyl, where the two last mentionedgroups may carry one to three of the following substituents: halogen,C₁-C₄-alkylthio or C₁-C₄-alkoxy; or is tetrahydropyran-2-yl,tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl,tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl,1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl,1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the 6 last mentionedradicals may be substituted by one to three C₁-C₄-alkyl radicals; R¹⁰ ishydrogen, C₁-C₄-alkyl or C₁-C₆-alkoxycarbonyl; or R⁸ and R¹¹ togetherform π bond or a three- to six-membered carbocyclic ring; or the CR⁸R⁹unit represents a C═O group.
 3. The 2-benzoylcyclohexane-1,3-dione offormula I defined in claim 1, wherein R¹ is nitro, halogen, cyano,thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl,C₂-C₆-alkynyl, —OR³ or —S(O)_(n)R³; R² is hydrogen or one of theradicals mentioned above under R¹.
 4. The 2-benzoylcyclohexane-1,3-dionedefined in claim 1 which is of formula Ia:


5. The 2-benzoylcyclohexane-1,3-dione of formula Ia defined in claim 4wherein X¹ is a C₁-C₃-alkylene, C₂-C₃-alkenylene or C₂-C₃-alkynylenechain which is interrupted by an oxygen.
 6. The2-benzoylcyclohexane-1,3-dione of formula Ia defined in claim 4 whereinHet is a five- or six-membered partially or fully saturated heterocyclicor a 5- or 6-membered heteroaromatic group having up to three nitrogenring members as hetero atoms.
 7. The 2-benzoylcyclohexane-1,3-dione offormula I defined in claim 1, wherein R¹ is nitro, halogen,C₁-C₆-haloalkyl, —OR³ or —SO₂R³.
 8. The 2-benzoylcyclohexane-1,3-dioneof formula I defined in claim 1, wherein R² is hydrogen, nitro, halogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl, —OR³ or —SO₂R³.
 9. The2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1, whereinR³ is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,C₂-C₃-alkynyl or phenyl, wherein the alkyl radicals may be partially orfully halogenated and/or may carry one to three of the following groups:hydroxyl, mercapto, amino, cyano.
 10. The 2-benzoylcyclohexane-1,3-dioneof formula I defined in claim 1, wherein n is 0 or
 2. 11. The2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1, whereinX¹ is a straight-chain or branched C₁-C₄-alkylene, a C₂-C₄-alkenylene ora C₂-C₄-alkynylene chain which is interrupted by a hetero atom selectedfrom the group consisting of oxygen and sulfur, and wherein thealkylene, alkenylene or alkynylene radicals may be partially halogenatedand/or may carry one to three of the following groups: —OR⁴, —OCOR⁴,—OCONHR⁴ or —OSO₂R⁴.
 12. The 2-benzoylcyclohexane-1,3-dione defined inclaim 11, wherein X¹ is ethylene, propylene, propenylene or propynylenechain which is interrupted by an oxygen atom.
 13. The2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1, whereinR⁴ is hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl.
 14. The2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1 whereinHet is a five- or six-membered partially or fully saturated heterocyclicor a 5- or 6-membered heteroaromatic group having up to three nitrogenring members as hetero atoms.
 15. The 2-benzoylcyclohexane-1,3-dione offormula I defined in claim 2 wherein Het is a five- or six-memberedpartially or fully saturated heterocyclic or a 5- or 6-memberedheteroaromatic group having up to three nitrogen ring members as heteroatoms.
 16. A process for preparing the 2-benzoylcyclohexane-1,3-dione offormula I defined in claim 1, which comprises acylating a substituted orunsubstituted cyclohexane-1,3-dione Q with an activated carboxylic acidIIIa or with a carboxylic acid IIIb,

wherein L¹ is a nucleophilically replaceable leaving group, andrearranging the acylation product, optionally in the presence of acatalyst, to a compound I.
 17. An activated carboxylic acid of formulaIIIa or a carboxylic acid of formula IIIb as defined in claim
 16. 18. Acomposition comprising a herbicidally effective amount of at least one2-benzoylcyclohexane-1,3-dione of formula I defined in claim 1 or anagriculturally useful salt of I and auxiliaries which are customarilyused for formulating crop protection agents.
 19. A process for preparingthe composition defined in claim 18, which comprises mixing aherbicidally effective amount of at least one2-benzoylcyclohexane-1,3-dione of formula I or an agriculturally usefulsalt of I and auxiliaries which are customarily used for formulatingcrop protection agents.
 20. A method for controlling unwantedvegetation, which comprises allowing a herbicidally effective amount ofat least one 2-benzoylcyclohexane-1,3-dione of formula I defined inclaim 1 or an agriculturally useful salt of I to act on plants, theirhabitat and/or on seeds.